Pyridine ketones useful as herbicides

ABSTRACT

Compounds of formula (I) in which the substituents are as defined in claim 1 are suitable for use as herbicides.

[0001] The present invention relates to novel herbicidally active pyridine ketones, to processes for their preparation, to compositions which comprise these compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.

[0002] Pyridine ketones having herbicidal action are described, for example, in WO 97/46530. We have now found novel pyridine ketones having herbicidal and growth-inhibiting properties.

[0003] The present invention thus provides compounds of the formula I

[0004] in which

[0005] each R independently is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂- C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, CC₁-CC₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkylamino, di-C₁-C₆alkylamino, C₁-C₆alkylaminosulfonyl, di-C₁-C₆alkylaminosulfonyl, —N(R₁)—S—R₂, —N(R₃)—SO—R₄, —N(R₅)—SO₂—R₆, nitro, cyano, halogen, hydro x y, amino, formyl, hydroxy-C₁-C₆alkyl, CC₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl, thiocyanato-C₁-C₆alkyl, cyano-C₁-C₆alkyl, oxiranyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkoxy-C₁-C₆alkoxy, cyano-C₁-C₆alkenyloxy, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkoxy, C₃C₆alkynyloxy, cyano-C₁-C₆alkoxy, C₁-C₆ alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy, alkoxycarbonyl-C₁-C₆alkylthio, alkoxycarbonyl-C₁-C₆alkylsulfinyl, alkoxycarbonyl-C₁-C₆alkylsulfonyl, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, where the phenyl groups may be mono- or polysubstituted by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or R is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is either attached directly to the pyridine ring or attached to the pyridine ring via a C₁-C₄alkylene group, and where each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and where the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₆alkylaminosulfonyl, C₁-C₆dialkylaminosulfonyl, C₁-C₆alkylene-R₇, NR₈R₉, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0006] m is 1, 2, 3 or 4;

[0007] p is 0 or 1;

[0008] R₁, R₃ and R₅ independently of one another are hydrogen or C₁-C₆alkyl;

[0009] R₂ is NR₁₀R₁₁, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆a lkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0010] R₄ is NR₁₂R₁₃, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0011] R₆ is NR₁₄R₁₅, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phpnyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0012] R₇ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0013] R₈, R₁₀, R₁₂ and R₁₄ independently of one another are hydrogen or C₁-C₆alkyl;

[0014] R₉, R₁₁, R₁₃ and R₁₅ is independently of one another are C₁-C₆alkyl or C₁-C₆alkoxy;

[0015] Q is the group Q₁

[0016] in which

[0017] R₁₆, R₁₇, R₁₈ and R₁₉ independently of one another are hydrogen, hydroxyl, C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂, C₁-C₆alkoxy, cyano, nitro, halogen or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or two adjacent substituents from the group consisting of R₁₆, R₁₇, R₁₈ and R₁₉ form a C₂-C₆alkyiene bridge;

[0018] R₂₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkeny isulfinyl, C₂-C₁₂alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsultonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(Q)O, H(C₁-C₄alkoxy)P(O)O,

[0019] R₃₇R₃₈N, R₇₁R₇₂NNH—, R₂₁R₂₂NC(O)O—, R₇₃R₇₄NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₃₉, C₁-C₆haloalkyl-S(O)₂NR₄₀, C₁-C₆alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzyisu lfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano,

[0020] or a group Ar₁-thio, Ar₂-su lfinyl, Ar₃-sulfonyl, —OCO—Ar₄ or NH—Ars in which Ar₁, Ar₂, Ar₃, Ar₄ and Ar₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆falkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosufonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₄₁, NR₄₂R₄₃, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0021] R₄₁ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0022] R₄₂ is hydrogen or C₁-C₆alkyl;

[0023] R₄₃ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0024] R₂₁, R₃₇, R₃₉, R₄₀, R₇₁ and R₇₃ independently of one another are hydrogen or C₁-C₄alkyl;

[0025] R₂₂, R₃₈, R₇₂ and R₇₄ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₂₁ and R₂₂ together or R₃₇ and R₃₈ together or R₇₁ and R₇₂ together or R₇₃ and R₇₄ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or are the group Q₂

[0026] in which

[0027] Y is a chemical bond, an alkylene group A l, carbonyl, oxygen, sulfur, sulfinyl, sulfonyl, —NHR₂₄₈ or NH(CO)R₂₄₉;

[0028] A₁ is C(R₂₄₆R₂₄₇)m₀₁,

[0029] A is C(R₂₄₄R₂₄₅)r;

[0030] r and m₀₁ independently of one another are 0, 1 or 2;

[0031] R₂₄₀ is hydrogen, methyl or C₁-C₃alkoxycarbonyl;

[0032] R₂₄₁, R₂₄₂, R₂₄₃, R₂₄₄, R₂₄₅, R₂₄₆ and R₂₄₇ independently of one another are hydrogen, halogen or methyl, or R₂₄₃ together with an adjacent group R₂₄₅ or R₂₄₇ is a chemical bond;

[0033] R₂₄₈ and R₂₄₉ independently of one another are hydrogen or C₁-C₄alkyl;

[0034] R₂₃ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenyisulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsultonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsuflonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O,

[0035] R₄₄R₄₅N, R₇₅R₇₆NNH—, R₄₆R₄₇NC(O)O—, R₇₇R₇₈NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₄₈, C₁-C₄haloalkyl-S(O)₂NR₄₉, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzyisulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenyisulfonyl, phenylsulfonyloxy or benzoyloxy . where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkyisulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano,

[0036] or a group Ar₆-thio, Ar₇-sulfinyl, Ar₈-sulfonyl, —OCO—Ar₉ or NH—Ar₁₀ in which Ar₆, Ar₇, Ar₈, Ar₉ and Ar₁₀ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₀, NR₅,R₅₂, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0037] R₅₀ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsultonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0038] R₅₁ is hydrogen or C₁-C₆alkyl;

[0039] R₅₂ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0040] R₄₆, R₄₄, R₄₈, R₄₉, R₇₅ and R₇₇ independently of one another are hydrogen or C₁-C₄alkyl;

[0041] R₄₇, R₄₅, R₇₆ and R₇₈ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₄₄ and R₄₅ together or R₄₆ and R₄₇ together or R₇₅ and R₇₆ together or R₇₇ and R₇₈ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or are the group Q₃

[0042] in which

[0043] R₂₆ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂ alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O,

[0044] R₅₃R₅₄N, R₇₉R₈₀NNH—, R₅₅R₅₆NC()O—, R₈₁R₈₂NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₅₇, C₁-C₄haloalkyl-S(O)₂NR₅₈, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzyithio, benzylsulfinyl, benzylsultonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano,

[0045] or a group Ar₁₁-thio, Ar₁₂-sulfinyl, Ar₁₃-sulfonyl, —OCO—Ar₁₄ or NH—Ar₁₅ in which Ar₁₁, Ar₁₂, Ar₁₃, Ar₁₄ and Ar₁₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkyny toxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsu ffinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosu ffonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₉, NR₆₀R₆₁, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0046] R₅₉ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0047] R₆₀ is hydrogen or C₁-C₆alkyl;

[0048] R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0049] R₅₅, R₅₃, R₅₇, R₅₈, R₇₉ and R₈₁ independently of one another are hydrogen or C₁-C₄alkyl; R₅₆, R₅₄, R₈₀ and R₈₂ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₅₃ and R₅₄ together or R₅₅ and R₅₆ together or R₇₉ and R₈₀ together or R₈₁ and R₈₂ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; R₂₉ is hydrogen, C₁-C₆alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, (C₁-C₄alkyl)NHCO, phenylaminocarbonyt, benzylaminocarbonyt or (C₁-C₄alkyl)₂NCO, where the phenyl and benzyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), hatogen, nitro or cyano;

[0050] or is the group Q₄

[0051] in which

[0052] R₃₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alky lsultonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkenyisulfinyl, C₂-C₁₂alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynyisulfinyl, C₂-C₁₂alkynyisulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsuffonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O,

[0053] R₆₂R₆₃N, R₈₃R₈₄NNH—, R₆₄R₆₅NC(O)O—, R₈₅R₈₆NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₆₆, C₁-C₄haloalkyl-S(O)₂NR₆₇, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenyisulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfony l, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C i-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano,

[0054] or a group Ar₁₆-thio, Ar trsu lfinyl, Ar₁₈-sulfonyl, —OCO—Ar₁₉ or NH—Ar₂₀ in which Ar₁₆, Ar₁₇, Ar₁₈, Ar₁₉ and Ar20 independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C ralkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acety oalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfony l, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₆₈, NR₆₉R₇₀, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0055] R₆₈ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsu lfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0056] R₇₀ is hydrogen or C₁-C₆alkyl;

[0057] R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0058] R₆₄, R₆₂, R₆₆, R₆₇, R₈₃ and R₈₅ independently of one another are hydrogen or C₁-C₄alkyl;

[0059] R₆₅, R₆₃, R₈₄ and R₈₆ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₆₂ and R₆₃ together or R₆₄ and R₆₅ together or R₈₃ and R₈₄ together or R₈₅ and R₈₆ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups;

[0060] R₃₃ and R₃₄ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsu lfonyl, C₁-C₄alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂, C₁-C₆alkoxy or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or R₃₃ and R₃₄ together form a C₂-C₆alkylene bridge; and

[0061] R₃₅ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl or benzyl, which for its part may be substituted by halogen, methyl or methoxy, or is C₁-C₄alkoxycarbonyl or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄aikoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsuitonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano;

[0062] or is the group Q₅

[0063] in which

[0064] Z is S, SO or SO₂;

[0065] R₀₁ is hydrogen, C₁-C₈alkyl, C₁-C₈alkyl substituted by halogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, —CO₂R₀₂, —COR₀₃, —COSR₀₄, —NR₀₅R₀₆, CONR₀₃₆R₀₃₇ or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHS)₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)S)₂—C₁-C₄alkyl, N(C₁-C₆alkyI)SO₂-phenyl, N(C₂-C₆alkenyl)S)₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)S)₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyt, N(C₃-C₇cycloalkyl)S)₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)S)₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OS)₂—C₁-C₄alkyl, CONR₂₅R₂₆, OS)₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenytthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsu lfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₁₅CO₂R₀₂₇;

[0066] or R₀₁ is C₂-C₈alkenyl or C₂-C₈alkenyl substituted by halogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, —CONR₀₃₂R₀₃₃, cyano, nitro, —CHO, —CO₂R₀₃₈, —COR₀₃₉, —COS—C₁-C₄alkyl, —NR₀₃₄R₀₃₅ or phenyl which for its part may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHS)₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)S)₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)S)₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)S)₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)S)₂—C₁-C₄alkyl, alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₀R₀₄₁, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsultonyl, phenylsultonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsuffinyl, C₁-C₄alkylene-phenyl or —NR₀₄₃CO₂R₀₄₂;

[0067] or R₀₁ is C₃-C₆alkynyl or C₃-C₆alkynyl substituted by halogen, C₁-C₄haloalkyl, cyano, —CO₂R₀₄₄ or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyt, OSO₂—C₁-C₄alkyl, CONR₀₂₈R₀₂₉, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsu ifonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₃₁CO₂R₀₃₀;

[0068] or R₀₁ is C₃-C₇cycloalkyl, C₃-C₇cycloalkyl substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or phenyl, which for its part may be substituted by halogen, nitro, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkyl and C₁-C₄haloalkyl; or

[0069] R₀₁ is C₁-C₄alkylene-C₃-C₇cycloalkyl, phenyl, or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₅R₀₄₆, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfo nyl, phenylsutfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, or —NR₀₄₈CO₂R₀₄₇; or

[0070] R₀₁ is C₁-C₄alkylene-phenyl, COR₀₇ or 4-6-membered heterocyclyl;

[0071] R₀₂, R₀₃₈, R₀₄₄ and R₀₆₆ independently of one another are hydrogen, C₁-C₄alkyl, phenyl, or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂-C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂-C₁-C₄alkyl, N(C₃-C cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₉R₀₅₀, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsuffonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haioalkylsulfinyl, phenylsultinyl, C₁-C₄alkylene phenyl or —NR₀₅₂CO₂R₀₅₃;

[0072] R₀₃, R₀₃₉ and R₀₆₇ independently of one another are C₁-C₄alkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇ cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONRO₀₇₀R₀₅₄, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₅₆CO₂R₀₅₅;

[0073] R₀₄ is C₁-C₄alkyl;

[0074] R₀₅ is hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂H, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂H, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₅₇R₀₅₈, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyi, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkyisulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylenephenyl or —NR₀₆₀CO₂R₀₅₉;

[0075] R₀₆ is hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄aikyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloaikyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₆₁R₀₆₂, OSO₂—C₁-C₄ haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₆₄CO₂R₀₆₃;

[0076] R₀₇ is phenyl, substituted phenyl, C₁-C₄alkyl, C₁-C₄alkoxy or —NR₀₈R₀₉;

[0077] R₀₈ and R₀₉ independently of one another are C₁-C₄alkyl, phenyl or phenyl which is substituted by halogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄thioalkyl, —CO₂R₀₆₆, —COR₀₆₇, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkyl; or R₀₈ and R₀₉ together form a 5-6-membered ring which may be interrupted by oxygen, NR₀₆₅ or S,

[0078] R₀₁₅, R₀₃₁, R₀₄₃, R₀₄₈, R₀₅₂, R₀₅₆, R₀₆₀ and R₀₆₄ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃C₆alkynyl or C₃-C₇cycloalkyl;

[0079] R₀₂₅, R₀₂₆, R₀₂₇, R₀₂₈, R₀₂₉, R₀₃₀, R₀₃₂, R₀₃₃, R₀₃₄, R₀₃₅, R₀₃₆, R₀₃₇, R₀₄₀, R₀₄₁, R₀₄₂, R₀₄₅, R₀₄₆, R₀₄₇, R₀₄₉, R₀₅₀, R₀₅₃, R₀₅₄, R₀₅₅, R₀₅₇, R₀₅₈, R₀₅₉, R₀₆₁, R₀₆₂, R₀₆₃, R₀₆₅ and R₀₇₀ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl, or phenyl which is substituted by halogen, nitro, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkyl or C₁-C₄haloalkyl; and

[0080] R₃₆ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or C₃-C₆cycloaikyl which is substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, di-C₁-C₄alkylamino, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O or phenyl which for its part may be substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, cyano, nitro or COOH; and agronomically acceptable salts M⁺ and all stereoisomers and tautomers of the compounds of the formula I.

[0081] The compounds of the formula I can be present in different isomeric forms which can be isolated in pure form. The invention therefore also embraces all stereoisomeric forms of the compound of the formula I. Examples of these isomeric forms are the formulae Ix, Ixx, Ixxx and Ixxxx below, in which Q is the group Q₂.

[0082] The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl and octyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

[0083] Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl.

[0084] Haloalkyl groups preferably have a chain length of from 1 to 8 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

[0085] Suitable haloalkenyl groups are alkenyl groups which are mono- or polysubstituted by halogen, halogen being fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en-1-yl. Among the C₃-C₂₀alkenyl groups which are mono-, di- or trisubs btuted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.

[0086] Suitable haloalkynyl groups are, for example, aikynyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and in particular fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluorobut-2-yn-1-yl. Among the alkynyl groups which are mono- or polysubstituted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.

[0087] Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyt, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Haloalkoxy groups preferably have a chain length of from 1 to 8 carbon atoms. Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 24luoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of from 1 to 8 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsuffinyl is, for example, methylsulfinyl, ethylsulfinyl, propyisulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfiny l, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl. Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsultonyl, sec-butylsulfonyl or tert-butylsu lfonyl; preferably methylsulfonyl or ethylsulfonyl. Alkoxyalkoxy groups preferably have a chain length of from 1 to 8 carbon atoms. Examples of alkoxyalkoxy groups are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy. Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Preference is given to alkylamino groups having a chain length of from 1 to 4 carbon atoms. Alkoxyalkyl groups have a chain length of preferably from 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl groups preferably have from 1 to 8 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, iso-propylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably have from 3 to 8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Phenyl, also as part of a substituent as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl, may be substituted. In this case, the substituents can be in ortho, meta and/or para position. The preferred substituent positions are the ortho and para positions to the ring attachment point. Heterocyclyl is to be understood as meaning ring systems which, in addition to carbon atoms, contain at least one heteroatom, such as nitrogen, oxygen and/or sulfur. They can be saturated or unsaturated. In the context of the present invention, heterocyclyl ring systems may also be substituted. Suitable substituents are, for example, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, cyano, nitro, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylthio or C₃-C₆cycloalkyl.

[0088] Heterocyclyl may be, for example, furyl, thiophenyl, pyrrolidyl, piperidinyl, morpholinyl, pyridyl, imidazolyl, tetrahydrofuryl, tetrahydropyranyl, dihydrofuryl, dihydropyranyl, isoxazolyl, oxazolyl, isothiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazo lyl, thiazolyl, pyrazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, tetrazolyl, pyrimidyl, pyrazinyl, sym. or unsym. triazinyl, piperazinyl, oxazolinyl (for example:

[0089] oxazolidinyl, imidazolinyl, imidazolidinyl, dioxanyl, oxetanyl, in particular 2-oxetanyl, or phthalimidyl.

[0090] The invention also embraces the salts M⁺ which can be formed by the compounds of the formula 1, in particular the compounds of the formula I in which R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl, preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal bases, the hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular those of sodium or potassium, may be especially emphasized as salt formers. Examples of amines suitable for ammonium salt formation are both ammonia and primary, secondary and tertiary C₁-C₁₈alkylamines, C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, al iylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amiines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine: primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, naphthylamines and o,m,p-chloroanilines; but in particular triethylamine, isopropylamine and diisopropylamine. Quatemary ammonium bases which are suitable for salt formation are, for example, [N(R_(a01) R_(b01) R_(c01) R_(d01))]⁺ OH⁻, where R_(a01), R_(b01), R_(c01) and R_(d01) independently of one anotheer are C₁-C₄alkyl. Further suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

[0091] Preferred compounds of the formula I correspond to the formula Ib

[0092] in which

[0093] each R independently is C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsu ffinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkylamino, di-C₁-C₆-alkylamino, C₁-C₆alkylaminosu ffonyl, di-C₁-C₆alkylaminosulfonyl, —N(R₁)—S—R₂, —N(R₃)—SO—R₄, —N(R₅)—SO₂—R₆, nitro, cyano, halogen, hydroxyl, amino, or a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is either attached directly to the pyridine ring or attached via a C₁-C₄alkylene group to the pyridine ring, and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-Csacetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃-alkylene-R₇, NR₈R₉, halogen, cyano, nitro, phenyl and benzylthio where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen;

[0094] Q is the group Q₁ in which

[0095] R₂₀ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy, C₁-C₄alkoxycarbonyloxy, R₂₁R₂₂N—C(O)O, phenylthio, C₁-C₄alky lthio, C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

[0096] R₂₁, and R₂₂ independently of one another are hydrogen or C₁-C₄alkyl; or the group Q_(2a)

[0097] in which R₂₃ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy, C₁-C₄alkoxycarbonyloxy, R₂₄R₂₅N—C(O)O, phenylthio, C₁-C₄alkylthio, C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄-alkyl(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

[0098] R₂₄ and R₂₅ independently of one another are hydrogen or C₁-C₄alkyl; and

[0099] Y is oxygen, sulfur, a chemical bond or a C₁-C₄alkylene bridge;

[0100] or the group Q₃

[0101] in which R₂₆ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy, C₁-C₄alkoxycarbonyloxy, R₂₇R₂₈N-C(O)O, phenylthio, C₁-C₄alkylthio, C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄-alkyl(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

[0102] R₂₇ and R₂₈ independently of one another are hydrogen or C₁-C₄alkyl and

[0103] R₂₉ is hydrogen, C₁-C₆alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, (C₁-C₄alkyl)NHCO or (C₁-C₄alkyl)₂NCO; or the group Q₄

[0104] in which R₃₀ is hydroxyl, C₁-C₄alkoxy, C₁-C₄alkylcarbonyloxy, C₁-C₄alkoxycarbonyloxy, R₃₁R₃₂N-C(O)O, phenylthio, C₁-C₄alkylthio, C₁-C₄alkyl-S(O)₂O, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄-alkyl(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O or benzoyloxy; and

[0105] R₃₁ and R₃₂ independently of one another are hydrogen or C₁-C₄alkyl;

[0106] R₃₃ and R₃₄ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C2-C₆alkynyl, C₁-C₄-alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂, C₁-C₆alkoxy, or phenyl which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₃₃ and R₃₄ together form a C₂-C₆alkylene bridge; and

[0107] R₃₅ is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxycarbonyl or phenyl which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₀-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or the group Q₅, and also agronomically acceptable salts of these compounds, the other substituents being defined as under formula I in claim 1. Among the compounds of the formula lb, preference is furthermore given to those in which the group

[0108] —C(O)—Q is located in the 3 position on the pyridine ring, or in which Q is Q₂, R₂₃ being, in particular, hydroxyl, Y being a methylene bridge and m being the number 2. Preference is further given to compounds of the formula lb in which R is C₁-C₆alkyl or C₁-C₆haloalkyl.

[0109] Preferred compounds of the formula I are characterized in that the group —C(O)Q is in the ortho position to a group R. Preference is furthermore given to compounds of the formula I in which a group R is C₁-C₆haloalkyl and in the ortho position to the pyridyl nitrogen. Of particular interest are furthermore compounds of the formula I in which the group —C(O)Q is in the 3 position to the pyridyl nitrogen. In the formula 1, p is preferably the number 0. Also to be emphasized are compounds of the formula I in which m is 2 and R is C₁-C₃alkyl, C₁-C₃-haloalkyl, C₁-C₂alkoxymethyl, C₁-C₂alkythiomethyl, hydroxymethyl, C₁-C₆alky lcarbonyloxymethyl, benzoyloxymethyl, C₁-C₄alkoxycarbonyloxymethyl, chlorine, cyano, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylsulfonyloxy, C₁-C₂alkylsulfinylmethyl or C₁-C₂alkylsulfonylmethyl. A further group of preferred compounds of the formula I is formed by those compounds in which at least one group R is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl.

[0110] Particularly noteworthy compounds of the formula I are those in which Q is a group Q₁ and R₁₆, R₁₈ and R₁₉ are C₁-C₃alkyl and R₁₇ is hydrogen, or Q is a group Q₂ and Y is —CH₂—, —CH₂CH₂— or oxygen, A is —CH₂— and R₂₄₀, R₂₄₁, R₂₄₂ and R₂₄₃ are Mch hydrogen, or Q is a group Q₃ and R₂₉ is C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl or C₁-C₄alkylaminocarbonyl or di(C₁-C₂-alkyl)aminocarbonyl, or Q is a group Q₄ in which R₃₃, R₃₄ and R₃₅ are C₁-C₃alkyl. In these noteworthy compounds of the formula I, R₂₀, R₂₃, R₂₆ and R₃₀ independently of one another are halogen, thiocyanato, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₂alkoxy, C₁-C₁₂-alkylthio, alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenylsulfonyl, C₂-C₁₂-haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₂-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₂alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₂alkylsulfonyl, C₁-C₄alkyl-S(O)₂NH, C₁-C₄haloalkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, C₂-C₁₈-alkenylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂-alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may in each case be substituted by C₁-C₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄-alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsuonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalky lsulfonyl, C₁-C₄-haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano, or R₂₀, R₂₃, R₂₆ and R₃₀ independently of one another are thienylcarbonyloxy or furylcarbonyloxy which for their part may be substituted by methyl or halogen, or are pyridylcarbonyloxy which for its part may be substituted as stated in claim 1, or R₂₀ is R₃₇R₃₇N, R₇₁R₇₂NNH—, R₂₁R₂₂NC(O)O— or R₇₃R₇₄NC(O)NH—; or R₂₃ is R₄₄R₄₅N, R₇₅R₇₆NNH—, R₄₆R₄₇NC(O)O— or R₇₇R₇₈NC(O)NH—; or R₂₆ is R₅₃R₅₄N, R₇₉R₈₀NNH—, R₅₅R₅₆NC(O)O— or R₈₁R₈₂NC(O)NH—; or R₃₀ is R₆₂R₆₃N, R₈₃R₈₄NNH—, R₆₄R₆₅NC(O)O— or R₈₅R₈₆NC(O)NH—. Very particularly preferably, R₂₀, R₂₃, R₂₆ or R₃₀ are hydroxyl or O⁻M⁺.

[0111] A further preferred group is formed by those compounds of the formula I in which Q is a group Q₅, R₃₆ is C₁-C₄alkyl, C₁-C₄haloalkyl or cyclopropyl and R₀₁ is C₁-C₆alkyl, C₁-C₄-alkoxycarbonylmethyl, C₃-C₈alkenyl, is benzyl or phenyl substituted by methyl, halogen, trifluoromethyl, methoxy, and at least one group R is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl located in the ortho position to the pyridyl nitrogen.

[0112] The process according to the invention for preparing compounds of the formula I

[0113] in which R and m are as defined under formula 1; p is 0 and Q is the group

[0114] is carried out analogous ly to known processes (for example those desc n ibed in WO 97/46530 and EP-A-0 353 187) and comp r ises

[0115] a) reacting a compound of the formula II

[0116]  in which R and m are as defined under formula I and X is a leaving group, for example halogen, in an inert organic solvent in the presence of a base with compounds of the formula III, IV,V or VI

[0117]  in which R₁₆, R₁₇, R₁₈, R₁₉,R₂₉, R₃₃, R₃₄, R₃₅, R₂₄₀, R₂₄₃, R₂₄₂, R₂₄₁, A and Y are as defined under formula I to give the compounds of the formula VII, VIII, IX or X

[0118]  and then isomerizing these compounds, for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a source of cyanide; or

[0119] b) reacting a compound of the formula Xi

[0120]  in which R and m are as defined under formula I with compounds of the formula III, IV, V or VI

[0121]  in which R₁₆, R₁₇, R₁₈, R₁₉, R₂₉, R₃₃, R₃₄, R₃₅, R₂₄₀, R₂₄₃, R₂₄₂, R₂₄₁, A and Y are as defined under formula I in an inert organic solvent in the presence of a base and a coupling agent to give a compound of the formula VII, VIII, IX or X

[0122]  and then isomerizing these compounds, for example as described under route a).

[0123] Compounds of the formula I in which R₂₀, R₂₃, R₂₆ and R₃₀ are different from hydroxyl or halogen can be prepared by converesion methods which are generally known from the literature, for example acyclations or carbamoylations with appropriate acyl chlorides, from compounds in which R₂₀, R₂₃, R₂₆ or R₃₀ is hydroxyl in the presence of a suitable base, or they can be prepared by nucleophilic substitution reactions on chlorides of the formula I in which R₂₀, R₂₃, R₂₆ or R₃₀ is halogen, which are likewise obtainable by known processes by reaction with a chlorinating agent, such as phosgene, thionyl chloride or oxalyl chloride. Here, for example, suitably substituted amines, or hydroxylamines directly, or alkylsulfonamides, mercaptans, thiophenols, phenols, Ar₁—NH₂ or Ar₁—SH, are employed in the presence of a base, for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.

[0124] Compounds of the formula I in which R₂₀, R₂₃, R₂₆ or R₃₀ comprise thio groups can be oxidized analogously to known standard processes, for example using peracids, for example meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding su lfones and sulfoxides of the formula I. Here, the degree of oxidation at the sulfur atom (SO— or SO₂—) can be controlled by the amount of oxidizing agent.

[0125] The process according to the invention for preparing compounds of the formula I in which R and m are as defined under formula I and Q is a group

[0126] in which Z is sulfur, q is 0 and R₃₆ and R₀₁ are as defined under formula I is carried out analogously to known processes (for example those described in WO 97/43270) and comprises converting a compound of the formula XII

[0127] in which R₃₆, R and m are as defined under formula I in the presence of a base, carbon disulfide and an alkylating agent of the formula XIII

R₀₁—X₁   (XIII),

[0128] in which R₀₁ is as defined under formula I and X₁ is a leaving group, for example halogen or sulfonate, into the compound of the formula XIV

[0129] in which Z is sulfur and R, R₀₁, R₃₆ and m are as defined above and then cyclizing this compound using hydroxylamine hydrochloride, in the presence or absence of a solvent, in the presence of a base to give the compounds of the formulae

[0130] in which Z is sulfur and R, R₃₆, R₀₁ and m are as defined above, and then oxidizing these compounds with an oxidizing agent, for example meta-chloroperbenzoic acid (m-CPBA). The isomers of the formulae le and If can be separated using column chromatography and a suitable mobile phase and then purified.

[0131] The preparation of the compounds of the formula I in which p is 0 is illustrated in more detail in the reaction schemes 1 and 2 below.

[0132] According to this reaction scheme, the compounds of the formula I with the group Q₁ in which R20 is hydroxyl, the compounds of the formula I with the group Q₂ in which R₂₃ is hydroxyl, the compounds of the formula I with the group Q₃ in which R₂₆ is hydroxyl and the compounds of the formula I with the group Q₄ in which R₃₀ is hydroxyl can preferably be prepared.

[0133] For preparing the compounds of the formula I in which Q is the groups Q₁ to Q₄ and R₂₀, R₂₃,R₂₆ and R₃₀ are hydroxyl, in accordance with reaction scheme 1, route a), the carboxylic acid derivatives of the formula II in which X is a leaving group, for example halogen, for example iodine, bromine and in particular chlorine, N-oxyphthali r nide or N,O— dimethylhydroxylamino or part of an activated ester, for example

[0134] (formed from dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or

[0135] (formed from N-ethyl-N′-(3-dimethyiaminopropyl)carbodiimide (EDC) and the corresponding carboxylic acid) are employed. These compounds are reacted in an inert organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, and in the presence of a base, for example an alkylamine, for example triethylamine, an aromatic amine, for example pyridine or 4-dimethyiaminopyridine (DMAP), with the dione derivatives of the formula III, IV, V or VI to give the isomeric enol ethers of the formulae Vl I, Vil, IX and X. This esterification is carried out at temperatures of from 0° C. to 110° C.

[0136] The isomerization of the ester derivatives of the formulae VII, VIII, IX and X to the dione derivatives of the formula I (in which R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl) can be carried out, for example, analogously to EP 369 803 in the presence of a base, for example an alkylamine, for example triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP or a cyanide source, for example acetone cyanohydrin or potassium cyanide.

[0137] According to reaction scheme 1, route b), the desired diones of the formula I (in which R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl) can be obtained, for example, in analogy to Chem. Lett. 1975, 1045 by esterifying the carboxylic acids of the formula Xl with the dione derivatives of the formula III, IV, V or VI in an inert solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, in the presence of a base, for example an alkylamine, for example triethylamine, and a coupling agent, for example 2-chloro-1-methylpyridinium iodide. Depending on the solvent used, this esterification is carried out at temperatures of from 0° C. to 110° C., affording initially, as described under route a), the isomeric ester of the formula I which can be isomerized as described under route a), for example in the presence of a base and a catalytic amount of DMAP, or a cyanide source, to give the desired dione derivative of the formula I (R₂₀, R₂₃, R₂₆ and R₃₀ are hydroxyl).

[0138] The preparation of the compounds of the formula I in which Q is the group Q₅ can be carried out in accordance with reaction scheme 2 by reacting the β-diketone derivative of the formula XII, for example in analogy to Synthesis 1991, 301; ibid. 1988, 793; or Tetrahedron 32, 3055 (1976) with carbon disulfide in the presence of a base, for example a carbonate, for example potassium carbonate, a metal hydride, for example sodium hydride, or potassium fluoride on aluminium, and an alkylating agent of the formula XIII in which X₁ is a leaving group, for example halogen, for example iodine, bromine and in particular chlorine,

[0139] This reaction is preferably carried out in the presence of a solvent, for example an amide, for example N,N-dimethylformamide (DMF), a sulfoxide, for example dimethylsulfoxide (DMSO), or a nit rle, for example acetonitrile. The ketene thioacetal of the formula XIV which is formed is cyclized with the aid of hydroxylamine hydrochloride in the presence of a base, for example sodium acetate, in a solvent, for example an alcohol, for example ethanol, or an ether, for example tetrahydrofuran, to give the compound of the formula le in which Z is sulfur. This cyclization reaction is carried out at temperatures of from 0° C. to 100° C. If appropriate, compounds of the formulae le and If (Z is sulfur) can be oxidized analogously to known standard processes, for example with peracids, for example meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formulae Ie and If (Z═SO— or SO₂—). Here, the degree of oxidation at the sulfur atom (Z═SO— or SO_(2—)) can be controlled by the amount of oxidizing agent.

[0140] Oxidations to the compounds of the formulae le and If (Z is SO— or SO_(2—)) are carried out as described, for example, in H.O. House, “Modern Synthetic Reactions” W. A. Benjamin, Inc., Menlo Park, Calif., 1972, pages 334-335 and 353-354.

[0141] The activated carboxylic acid derivatives of the formula II in reaction scheme 1 (route a) in which X is a leaving group, for example halogen, for example bromine, iodine or in particular chlorine, can be prepared by known standard processes, as described, for example, in C. Ferri “Reaktionen der organischen Synthese” [Reactions of Organic Synthesis], Georg Thieme Verlag, Stuttgart, 1978, page 461 ff. T his is shown in reaction scheme 3 below.

[0142] According to reaction scheme 3, the compounds of the formula II (X=Ieaving group) or II (X=halogen) are prepared, for example, by employing a halogenating agent, for example a thionyl halide, for example thionyl chloride or thionyl bromide; a phosphorus halide or phosphorus oxyhalide, for example phosphorus pentachloride or phosphorus oxychloride or phosphorus pentabromide or phosphoryl bromide; or an oxalyl halide, for example oxalyl chloride, or by employing a reagent for the formation of activated esters, for example N,N′-dicyclohexylcarbodiimide (DCC) or N-ethyl-N′-(3-dimethylaminopropyli)carbodiimide (EDC) of the formula X. For the compound of the formula X used as halogenating agents, X is a leaving group, for example halogen, for example fluorine, bromine or iodine and in particular chlorine, and W₁ is, for example, PCI₂, SOCI, SOBr or CICOCO. The reaction is carried out in the presence or absence of an inert organic solvent, for example in aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbons, for example n-hexane, benzene, toluene, xylenes, dichloromethane, 1,2-dichloroethane or chiorobenzene, at reaction temperatures in the range of from −20° C. to the reflux temperature of the reaction mixture, preferably at 40-150° C., and in the presence of a catalytic amount of N,N-dimethylformamide. Such reactions are generally known and described in the literature in various variations with respect to the leaving group X.

[0143] The compounds of the formulae III, IV, V and VI are known and can be prepared analogously to the methods described, for example, in WO 92/07837, DE-A-3818958, EP-A-0 338 992 and DE-A-3902818.

[0144] The compounds of the formula XII in reaction scheme 2 can be obtained by standard processes, for example from the corresponding compounds of the formula II

[0145] in which R and m are as defined above and X is a leaving group, for example halogen, for example via Claisen condensation, or from the compounds of the formula II by reaction with a ketocarboxylic acid salt of the formula XV

[0146] in which R36 is as defined under formula I and M⁺ is an alkali metal ion (cf., for example, WO 96/26192).

[0147] The compounds of the formulae II and XI are known and can be prepared analogously to the methods described, for example, in WO 97146530, EP-A-0 353 187, Heterocycles, 48, 779 (1998), Heterocycles, 46, 129 (1997), or Tetrahedron Letters, 1749 (1998).

[0148] For preparing all other compounds of the formula I functionalized according to the definition of (R)_(m), there is a large number of known standard processes available, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, and the choice of the suitable preparation processes depends on the properties (reactivities) of the substituents in the intermediates in question.

[0149] All further compounds originating from the scope of the formula I can be prepared in a simple manner, taking into account the chemical properties of the pyridyl or Q moiety.

[0150] The end products of the formula I can be isolated in a customary manner by concentration or evaporation of the solvent and be purified by recrystallization or trituration of the solid residue in solvents in which they are only sparingly soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by means of column chromatography and a suitable mobile phase.

[0151] Furthermore, it is known to the person skilled in the art in which order certain reactions have to be carried out advantageously to avoid possible side reactions. Unless a targeted synthesis is carried out for isolating pure isomers, the product may be obtained as a mixture of two or more isomers. The isomers can be separated by methods known per se.

[0152] Compounds of the formula I in which p is 1, i.e. the corresponding N-oxides of the formula I, can be prepared by reacting a compound of the formula I in which p is 0 with a suitable oxidizing agent, for example with the H₂O₂ urea adduct, in the presence of an acid anhydride, for example trifluoroacetic anhydride. This reaction sequence is demonstrated using the example of group Q₂ below:

[0153] Compounds of the formula I in which R in the ortho position to the pyridine nitrogen is 1 -chloro-C₁-C₂alkyl, 1-hydroxy-C₁-C₂alkyl, 1-(C₁-C₆alkylcarbonyloxy)-C₁-C₂alkyl, 1 -benzoyloxy-C₁-C₂alkyl, 1-(C₁-C₄alkoxycarbonyloxy)-C₁-C₂alkyl, 1-(C₁-C₄alkylthio)-C₁-C₂alkyl, 1-(C₁-C₄-alkylsulfinyl)-C₁-C₂alkyl, 1-(C I-C₄alkylsultonyl)-C₁-C₂alkyl, 1-thiocyanato-C₁-C₂alkyl, 1-cyano-C₁-C₂alkyl, can also be prepared, for example, by heating an N-oxide of the formula I under known reaction conditions, for example in the presence of tosyl chloride (see, for example, Parham, W. E.; Sloan, K. B.; Reddy, K. R.; Olson, P. E.; J Org Chem 1973, 38, 927) or in the presence of an acid anhydride (see, for example, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.; Heterocycles 1986, 24, 2169), followed, if appropriate, by subsequent conversion.

[0154] The compounds of the formula XXIIa are synthesized analogously to known processes, for example those mentioned in Heterocycles, 46, 129 (1997) or Helvetica Chimica Acta 71, 596 (1988), and comprises either

[0155] a) acylating a compound of the formula XVI

[0156] in which R₃₀₁ is hydrogen or C₁-C₆alkyl;

[0157] R₄₀₁ is hydrogen, C₁-C₆alkyl C₂-C₆alkenyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkyl, 1-(C₁-C₆alkylcarbonyloxy)-C₁-C₆alkyl, 1-(C₁-C₆alkylthio)-C₁-C₆-alkyl, 1-(C₁-C₆alkylsulfinyl)-C₁-C₆alkyl, 1-(C₁-C₆alkylsulfonyl)-C₁-C₆alkyl, 1-thiocyanato-C₁-C₆-alkyl, 1-cyano-C₁-C₆alkyl, phenyl, where the phenyl groups may be mono- or polysubstituted by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or is a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is either attached directly or via a C₁-C₄alkylene group to the double bond, and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms and the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxya lkyithio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₈₇, NR₈₈R₈₉, halogen, cyano, nitro, phenyi and benzylthio, where pheny l and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro and where substituents on nitrogen in the heterocyclic ring are different from halogen;

[0158] R₈₇ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0159] R₈₈ is hydrogen or C₁-C₆alkyl and

[0160] R₈₉ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0161] with a compound of the formula XVII

[0162] in which R₅₀₁ is C₁-C₆haloalkyl and X₂ is O(CO)R₅₀₁ or halogen to give the compound of the formula XVIII

[0163] in which R₃₀₁, R₄₀₁, R₅₀₁, and R₁₄ are as defined above, in the presence of a base, for example an aromatic amine, for example pyridine, and subsequently replacing the alkoxy group by the amino group using ammonia in an organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, or a nitrile, for example acetonitrile. The resulting compound of the formula XIX

[0164] is subsequently condensed with a compound of the formula XX

[0165] in which R₂₀₁ is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆-haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, 1-(C₁-C₆alkylcarbonyloxy)-C₁-C₆alkyl, 1-(C₁-C₆alkylthio)-C₁-C₆alkyl, 1-(C₁-C₆alkylsulfinyl)-C₁-C₆alkyl, 1-(C₁-C₆alkylsulfonyl)C₁-C₆alkyl, 1-thiocyanato-C₁-C₆alkyl, 1-cyano-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy, phenyl, benzyl, phenoxy, phenylthio, phenylsulfinyl, phenylsu ffonyl, benzyithio, benzylsulfinyl or benzylsulfonyl, where the phenyl gro y )ps may be mono- or polysubstituted at least by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or is a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached either directly or via a C₁-C₄-alkylene group and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆a lkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalky lsulfinyl, C₁-C₆alkylsu lfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃-R₉₀, NR₉₁R₉₂, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro, and where substituents on nitrogen in the heterocyclic ring are different from halogen;

[0166] R₉₀ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsuffinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃-alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0167] R₉₁ is hydrogen or C₁-C₆alkyl and

[0168] R₉₂ is C₁-C₆alkyl or C₁-C₆alkoxy and

[0169] R₁₄ is as defined above, and the resulting compound of the formula XXIa

[0170]  is subsequently hydrolysed to give the compound of the formula XXIIa

[0171]  in which R₂₀₁, R₃₀₁, R₄₀₁, and R₅₀₁ are as defined above, or

[0172] b) condensing a compound of the formula XXIII

[0173]  in which R₁₄ is as defined above with a compound of the formula XXIV

[0174]  and chlorinating the resulting compound of the formula XXV

[0175]  in which R₃₀₁, R₄₀₁ and R₅₀₁ are as defined above and R₁₄ is C₁-C₄alkyl to give compounds of the formula XXVI

[0176]  in which R₃₀₁, R₄₀₁, R₅₀₁ and R₁₄ are as defined above (using, for example, POCI₃), and subsequently reacting this compound with a nucleophile of the formula XXVII

Z—R₁₅₀   (XXVII)

[0177] In which Z is SH, OH or amino and R₁₅₀ is C₁-C₆alkyl, C₃-C₆alkeny4 C₃-C₆halogenalkenyl, C₃C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl, phenyl, benzyl, where the phenyl and benzyl groups for their part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, is C₁-C₁alkoxy-C₁-C₄alkyl or C₁-C₄-alkylthio-C₁-C₄alkyl, C₁-C₄alkylsulfinyl-C₁-C₄alkyl, C₁-C₄alkylsulfonyl-C₁-C₄alkyl, or a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆-alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆-alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃-alkylene-R₉₃, NR₉₄R₉₅, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃-haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on nitrogen in the heterocyclic ring are different from halogen;

[0178] R₉₃ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0179] R₉₄ is hydrogen or C₁-C₆alkyl and

[0180] R₉₅ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0181] in the presence of a base to give compounds of the formula XXIb

[0182] in which R₁₄, R₁₅₀, R₃₀₁, R₄₀₁, and R₅₀₁ are as defined above, and subsequen tly hydrolysing the resulting compound to give the compound of the formula XXIIb

[0183] in which R₁₅₀, R₃₀₁, R₄₀₁ and R₅₀₁ are as defined.

[0184] Compounds of the formula XXIb in which R l w is fluorine are prepared by reacting a compound of the formula XXVI in the presence of a polar aprotic solvent, for example acetonitrile, dimethylformamide or sulfolane, with potassium fluoride in the presence or absence of a catalytic amount of 18-crown-6. Compounds of the formula XXIc in which R₁₅₀ is hydrogen are preparerd by reducing the chlorine group in the formula XXVI, for example using hydrogen in the presence of a suitable metal catalyst or using ammonium formate in a suitable solvent. The preparation of the compounds of the formula XXIIa, or XXIIb and XXIIc is illustrated in more detail in the reaction schemes 4 and 5 below.

[0185] For preparing all other compounds of the formula I which are functionalized according to the definition of R₂₀₁ (R₁₅₀) to R₅₀₁, a large number of known standard processes is suitable, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of the suitable preparation processes depending on the properties (reactivities) of the substituents in the intermediates in question.

[0186] The novel compounds of the formula l ib in which R_(f) is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichloromethyl, R_(X1) is C₁-C₆alkyl and Q and R are as defined under formula I can be prepared by generally known processes via 3-alkoxycarbonyl-4-perhaloalkylpyridine N-oxides of the formula XXVIII according to reaction scheme 5 by preparing, using suitable chlorination conditions and separation processes, the 6-chloro-4-haloalkyl-3-nicotinic esters of the formula XXX and then converting these compounds with a nucleophile of the formula XXXI

Z₀₁—R_(151 tm (XXXI))

[0187] in which Z₀₇ is SH, hydroxyl, halogen or amino and R₁₅₁ is hydrogen, C₁-C₆aIkyl, C₃-C₆-alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, halogen, C₃-C₆haloalkynyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkyl, phenyl, benzyl, where the phenyl and benzyl groups for their part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C ,-C₃haloalkoxy, halogen, cyano or nitro, is C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C ~alkylthio-C₁-C₄alkyl , Ct-C₄alkylsulfinyl-C₁-C₄alkyl, C₁-C₄alkylsulfonyl-C₁-C₄alkyl, or a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system for its part may be mono-, di- or trisubstituted by

[0188] C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆-haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C a-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₀C₄cyanoalkylthio, C_(l)-C₆-alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R96, NR97R₉₈, halogen, cyano, nitro, phenyl or benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro,

[0189] R₉₆ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

[0190] R₉₇ is hydrogen or C₁-C₆alkyl and

[0191] R₉₈ is C₁-C₆alkyl or C₁-C₆alkoxy;

[0192] and where substituents on nitrogen in the heterocyclic ring are different from halogen, using reaction processses which are generally known to the person skilled in the art, into the 6-substituted 4-perhaloalkylnicotinic acids of the formula XXXII and their subsequent products of the formulae lIb and lb as described in reaction scheme 1. This is shown in reaction scheme 6 below.

[0193] According to this reaction scheme, it is preferably possible to prepare the compounds of the formula I with the group Q₁ in which R₂₀ is hydroxyl, the compounds of the formula I with the group 02 in which R23 is hydroxyl, the compounds of the formula I with the group Q₃ in which R₂₆ is hydroxyl and the compounds of the formula I with the group Q₄ in which R₃₀ is hydroxyl.

[0194] 6-substituted 2-haloalkylnicotinic acid compounds of the formula Ic can be prepared, for example, from the corresponding 2-haloalkyl-3-alkoxycarbonyl-2-pyridines XXXIII in which R_(f) is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichioromethyl and R_(1x) is C₁-C₆alkyl and R is as defined under formula I, by hydrolysis into the corresponding carboxylic acids and their subsequent activation, for example by conversion into an acylhalide (IIc). (Reaction scheme 7).

[0195] thier precursors of the formulae XXXIIIa, XXXIIIb, XXXIIIc, XXXIIId, XXXIIIe, XXXIIIf, XXXIIIg and XXXIIIh are likewise accessible by conversion processes known to the person skilled in the art (reaction shceme 7). 2-Trifluoromethyl-3-ethoxycarbonyl-2-pyridone (formula XXXIIIa in which R is hydrogen, R_(1X) is ethyl and Rf is trifluoromethyl) in particular is known form Org. Process Research & Developmnet, 1, 370 (1997).

[0196] Intermediates of the formulae XXXIIIa to XXXIIIh can be obtained by reacting, for example for preparing a 6-halo derivative of the formula XXXIIId, a pyridone of the formula XXXIIIa (preparation according to Org. Process Research & Development, 1, 370 (1997) or scheme 8) with a halogenating agent, for example phosphorus oxychloride, phosphorus oxybromide or phenyl dichlorophosphate, in the presence or absence of added base, such as a dialkylaniline, in the presence or absence of solvent, if desired in a pressure vessel, at temperatures between 0 and 220° C. (preferably 60-200° C.). It is known to the person skilled in the art how to convert chloro derivatives by nucleophilic substitution, for example using an alkali metal iodide in an inert solvent into the corresponding iodides, or using gaseous hydrobromic acid in lower carboxylic acids, for example conc. acetic acid, into the corresponding bromo derivatives (for example according to U.S. Pat. No. 3,974,166) or using alkali metal fluoride in a dipolar solvent, such as sulfolane, into the corresponding fluoro derivatives.

[0197] The compound of the formula XXXIIIe can be prepared by reacting a halo derivative of the formula XXXIIId obtained as described above with an alcohol of the formula R₁₅₁—OH in the presence of a base, such as sodium hydride, or an alkali metal oxide or carbonate, or directly with an alkali metal alkoxide, in an inert solvent such as dimethylformamide or in an excess of the alcohol of the formula R₁₅₁—OH which corresponds to the group to be introduced, at temperatures between −5 and 160° C., or by reacting, to prepare a corresponding 6-thioether of the formula XXXIIIc, analogously to what was described above, either the halide of the formula XXXIIId with a thiol of the formula R₁₅₁—SH in the presence of a base such as sodium hydride or with an alkali metal salt of a thiol in an inert solvent at −10-150° C., or by preparing, starting from a pyridone XXXIIIa and using a thionating agent, for example Lawesson's reagent, in an inert solvent, such as toluene or acetonitrile, a pyrithione of the formula XXXIIIb and alkylating this with an alkylating agent R r₁,-X, where X is a leaving group, such as halide (Cl, Br, I) or ROSO₃— or RSO₂—, at 20-120° C. in an inert solvent, such as tetrahydrofuran, to give the thioether of the formula XXXIIIc, or, to prepare the corresponding sulfinyl or su lfonyl derivative of the formula XXXIIIf, reacting with an oxidizing agent, such as m-chloroperbenzoic acid or sodium periodate, or sodium perborate, under temperature control known to the person skilled in the art, depending on the degree of oxidation (for example −30° C.-+50° C. for m₀₁=1 or −20° C.-+100° C. for m₀₁=2) in an inert solvent, such as dichloromethane, to give XXXIIIf, or, to prepare 6-alkyl derivatives XXXIIIg according to the invention, reacting a sulfone of the formula XXXlif (m₀₁=2) or a halo derivative of the formula XXXIIId in the presence or absence of a Pd(O) catalyst such as Pd(PPh₃)₂Cl₂ with a tetra-C₁-C₆alkyltin or with a Grignard reagent C₁-C₆alkyl-MgHal at temperatures between −10° and 180° C., for example analogously to Synlett 1998 (1185), or as described in Organocopper Reagents, R. J. K. Taylor, Oxford University Press 1994, or in Transition Metals in Organic Synthesis, S. Gibson, Oxford Univ. Press,1997, or in Org. React. 50, 1 (Stille reaction), or, to prepare 6-cyano derivatives of the formula XXXIIIh, reacting a halide of the formula XXXIIId or a sulfone of the formula XXXIIIf (m₀₁=2) with an alkali metal or tetraalkylammonium cyanide or copper cyanide in an inert solvent, such as dichloromethane, tetrahydrofuran or dimethylformamide, at temperatures between 0° C. and 220° C.

[0198] Some of the compounds of the formula XXXIIIe are also obtainable from the pyridone of the formula XXXIIIa by reacting them analogously to Org. React. 42, 2 with an alcohol R₁₅₁OH in the presence of an azodicarboxylic ester (for example diethyl ester) and triphenylphosphine in an inert solvent, such as tetrahydrofuran or dioxane. (Scheme 9)

[0199] The intermediates of the formula XXXIIIa required in reaction scheme 8 as starting materials are obtainable according to Scheme 10 route A or route B (Org. Process Research & Development, 1, 370 (1997)) or route C.

[0200] Intermediates of the formula XXXIIIa are obtainable by route A by reacting, to prepare the 3,4-dihydro-5-alkoxycarbonyl-6-haloalkylpyridin-2-ones of the formula XXXVIII, an enamine of the formula XXXV in the presence or, preferably, in the absence of a solvent either in an excess of enamine or in the presence of a base, such as a tert-amine, with an acryloyl chloride of the formula XXXIV at temperatures between −10° and +200° C., or by reacting a keto ester of the formula XXXVII with an acrylamide of the formula XXXVI in the presence of a catalyst such as p-toluenesulfonic acid (=HOTs) in an inert solvent, such as toluene, at temperatures between 30 and 200° C., with removal of the water of reaction formed (for example azeotropic distillation), or by reacting a keto ester of the formula XXXVII in the presence of a base, such as an alkali metal alkoxide or magnesium alkoxide, with a 4-haloketo ester of the formula XXXIX in an inert solvent, such as ethanol, at 0-180° C. to give the intermediate of the formula XXXX, converting this with ammonia or an ammonium salt, such as ammonium acetate, or with a bis-silylamine such as hexamethyldisilazane, in the presence or absence of an acidic catalyst, such as sulfuric acid or p-toluenesulfonic acid or an organic carboxylic acid (for example conc. acetic acid), in an inert solvent and at temperatures between 0° and 180° C. into the corresponding enamine of the formula XXXXI, subsequently cyclizing in the presence of a catalyst, such as p-toluenesulfonic acid or sulfuric acid, if desired with continuous removal of the water of reaction formed in an inert solvent, such as toluene, to give the dihydropyridone of the formula XXXVIII, and finally treating with an oxidizing agent, such as manganese dioxide, in an inert solvent, such as chlorobenzene, at temperatures between 50 and 250° C., to prepare the pyridones XXXIIIa.

[0201] The intermediates of the formula IIa

[0202] in which Q_(a) is hydroxyl, halogen, cyano, or a group —CH₂(CO)R₃₆ or

[0203] R_(b) is hydrogen, C₁-C₄alkyl or halogen;

[0204] R₁ is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichloromethyl;

[0205] R_(a) is C₁-C₃alkyl, C₁-C₃haloalkyl, C₃-C₄cycloalkyl, C₁-C₂alkoxy-C₁-C₄alkyl, C₁-C₂-alkylthiomethyl, hydroxyl, halogen, cyano, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyioxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or C₁-C₃alkylsulfonyloxy, and R₀₁ and R₃₆ are as defined under group O5 of the formula 1, except for the compounds 2,6-bistrifluoromethyinicotinic acid, 2,6-bistrifluoromethyl-5-methoxynicotinic acid and 2-hydroxy-6-trifluoromethyinicotinic acid, are novel and therefore likewise form part of the subject matter of the present invention.

[0206] Compounds of the formula IIb

[0207] in which Q_(b) is hydroxyl, halogen, cyano or a group —CH₂(CO)R₉₉ or

[0208] R₉₉ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃C₄cycloalkyl or C₁-C₄alkoxy;

[0209] R_(f) is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl; and

[0210] R_(c) is C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₂alkoxymethyl, C₁-C₁alkylthiomethyl, hydroxyl, halogen, cyano, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio, C₁-C₃-alkylsulfinyl, C₁-C₃alkylsulfonyl or C₁-C₃alkylsulfonyloxy and R₀₁ is as defined under formula I are novel and therefore likewise form part of the subject matter of the present invention.

[0211] Preferred compounds of the formula Ila correspond to the formula Ia

[0212] in which Q_(a) is hydroxyl, halogen , cyano or a group —CH₂(C₁)R₃₆ or

[0213] R₀₁ and R₃₆ are as defined in claim 1 and R_(a) is C₁-C₃alkyl.

[0214] The compounds of the formula I or compositions comprising them can be used according to the invention in all the application methods customary in agriculture, for example pre-emergence application, postemergence application and seed dressing, and various methods and techniques, for example controlled release of active compounds. To this end, the active compound is absorbed in solution onto mineral granule carriers or polymerized granules (urea/formaldehyde) and dried. If appropriate, a coating which allows the active compound to be released in metered form over a certain period of time can additionally be applied (coated granules).

[0215] The compounds of the formula I can be employed as herbicides in unchanged form, i.e. as they are obtained in the synthesis, but they are preferably processed in a customary manner with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. The methods of application, such as spraying, atomizing, dusting, wetting, scattering or watering, in the same way as the nature of the compositions, are chosen according to the aims striven for and the given circumstances.

[0216] The formulations, i.e. the compositions, formulations or preparations comprising the active compound of the formula I or at least one active compound of the formula I and as a rule one or more solid or liquid formulation auxiliaries, are prepared in a known manner, for example by intimate mixing and/or grinding of the active compounds with the formulation auxiliaries, for example solvents or solid carriers. Surface-active compounds (surfactants) can furthermore additionally be used during the preparation of the formulations. Examples of solvents and solid carriers are given, for example, in WO 97/34485 on page 6. Depending on the nature of the active compound of the formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.

[0217] Examples of suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.

[0218] The surfactants conventionally used in the art of formulation and which are suitable to prepare the herbicidal compositions according to the invention are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual”, MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant handbook], Carl Hanser Verag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.

[0219] The herbicidal formulations as a rule comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated compositions are rather preferred as commercial goods, the end user as a rule uses dilute compositions. The compositions can also comprise further additives, such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active compounds.

[0220] The active compounds of the formula I are as a rule applied to the plants or their habitat, at application rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg tha. The dosage required for the desired effect can be determined by tests. It depends on the nature of the effect, the development stage of the crop plant and the weed and on the application (location, time, process) and can, as a function of these parameters, vary within wide ranges.

[0221] The compounds of the formula I have herbicidal and growth-inhibiting properties, owing to which they can be used in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantings, rapeseed, maize and rice, and for the non-selective control of weeds. Crops include those which have been rendered tolerant towards herbicides or herbicide classes by conventional breeding methods or genetical engineering methods. The weeds to be controlled can be both monocotyledonous and dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria,Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

[0222] The examples below illustrate the invention in more detail, without limiting it.

PREPARATION EXAMPLES Example H1 PreParation of 2-difluoromethoxy-6-trifluoromethylnicotinic acid

[0223] At 70° C., 25 g (0.106 mol ) of (3-(ethoxycarbonyl)-6-trifluoromethyl)pyrid-2-one (Helv. Chim. Acta (1988), 71(3), 596 601) in a mixture of 50 ml of dimethylformamide and 20 ml of water are treated, in the presence of 16 g (0.116 mol) of finely powdered potassium carbonate and with efficient stirring, with a continuous stream of gaseous Freon-22. After 6 hours, a further 16 g of potassium carbonate and 20 ml of dimethyl sulfoxide are added, and the mixture is stirred with continuous introduction of Freon-22 gas at a temperature of 100° C for another 4 hours. The mixture is then treated with water and ice and extracted with diethyl ether. The aqueous phase is adjusted to pH 2 using conc. HCl and extracted with ethyl acetate. Diethyl ether is added to the extract, and some (3-(carboxy)-6-trifluoromethyl)pyrid-2-one crystals which have precipitated out are removed by filtration. The filtrate is filtered through a silica gel column (mobile phase ethyl acetate/hexane 1:1) giving, as a crystalline product, pure 2-difluoromethoxy-6-trifluoromethylnicotinic acid: ¹H NMR (CDCl₃, ppm): 8.60, d, J=9 Hz, 1H; 7.62, d, J=9 Hz, 1H; 7.62, t, J=67 Hz, 1H.

Example H2 Preparation of 4-methyl-6-trifluoromethylnicotinic Acid

[0224] In the presence of 5.8 ml of phenyl dichlorophosphate, 7.5 g (0.03 mol) of ((3-ethoxycarbonyl)-4-methyl-6-trifluoromethyl)pyrid-2-one (Helv. Chim. Acta (1988), 71 (3), 596-601) are heated in a pressure vessel at a temperature of 170° C. for 3 hours. The cold reaction solution is filtered directly through a short silica gel column (mobile phase: ethyl acetate/hexane 1:9), giving, as an oily product, ethyl 2-chloro-4-methyl-6-trifluoromethylpyridin-3-ylcarboxylate:

[0225]¹H NMR (CDCl₃, ppm): 7.49, s, 1H; 4.48, q, 2H; 2.43, s, 3H, 1.43, t, 3H.

[0226] 3.0 g (16.8 mmol) of the above product and, in 2 portions, a total of 5 g of ammonium formate are added to a suspension of 0.55 g of 10% Pd/C in 20 ml of methanol, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is then filtered through Celite and, after addition of sodium chloride solution, extracted with ethyl acetate. Chromatographic purification (mobile phase 1:9) gives the 4-methyl-6-trifluoromethylpyridin-3-yl ethyl ester as an oil: ¹H NMR (CDCl₃, ppm): 9.11, s, 1H; 7.56, s, 1H, 4.44, q, 2H; 2.72, s, 3H, 1.42, t, 3H. This is hydrolysed at 40° C. in the presence of aqueous potassium hydroxide solution in dioxane. Extraction with ethyl acetate gives, after acidification to pH 2.7, 4-methyl-6-trifluoromethyinicotinic acid as a crystalline product: ¹H NMR (CDCl₃, ppm): 7.49, s, 1H; 4.48, q, 2H; 2.43, s, 3H, 1.43, t, 3H; 9.32, s, 1 H, 7.62, s, 1 H, 2.79, s, 3H.

Example H3 Preparation of 6-chloro-4-trifluoromethylnicotinic Acid

[0227] 9.6 g (0.047 mol) of methyl 4-trifluoromethylpyridin-3-ylcarboxylate, dissolved in 50 ml of dichloromethane, are treated with 30% hydrogen peroxide/urea adduct and 17 ml of trifluoroacetic anhydride. The reaction solution is stirred at temperature of 20° C. for 20 hours and then washed once each with dilute sodium hydroxide solution and half-saturated sodium chloride solution. The product obtained is 3-methoxycarbonyl4-trifluoromethyl-3-pyridine N-oxide; ¹H NMR (CDCl₃, ppm): 8.55, s, 1H; 8.31, d, 1H; 7.6, d, 1H; 3.98, s, 3H. 4.85 g (0.022 mol) of the above product are then added to a mixture of 5 ml of phosphorus oxychloride and 4.3 ml of ethyidiisopropylamine in 15 ml of 1,2dichloroethane, and the mixture is heated to a temperature of 60° C. After about 2 hours, another 2 ml of phosphorus oxychloride and 2.8 ml of ethyidiisopropylamine are added, and the mixture is stirred at this temperature for 20 hours. The reaction mixture is subsequently added to ice-water, adjusted to pH 3 using 30% NaOH and then extracted with dich ioromethane. Filtration through a little silica gel gives an approximately 5:1 product mixture of the two 6-chloro- and 2-chloro-4-trifluoromethylpyridin-3-yl methyl esters, which can be separated by HPLC into the pure components. Thus, pure methyl 6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is obtained as the main product; ¹H NMR (CDCl₃, ppm): 8.91, s, 1H; 7.68, s, 1H; 3.98, s, 3H, and pure methyl 2-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is obtained as the byproduct; ¹H NMR (CDCl₃, ppm): 8.64, d, 1H; 7.52, d, 1H; 4.01, s, 3H. In the presence of 0.073 g of potassium hydroxide, 0.22 g of pure methyl 6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate are hydrolysed at room temperature in a 1:1 mixture of 6 ml of dioxane/water. Recrystallization gives the pure 6-chloro-4-trifluoromethyinicotinic acid: m.p. 115-117° C.; ¹H NMR (CDCl₃, ppm): 9.12, s, 1H; 7.24, s, 1H.

Example H4 Preparation of 6-methylthio-4-trifluoromethyinicotinic Acid

[0228] In boiling acetone, 0.70 g (2.9 mol) of methyl 6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is treated in the presence of a catalytic amount of 18-crown-6 with methanethiolate (0.33 g) until no further conversion can be detected by gas chromatographic analysis. The mixture is then filtered through silica gel and evaporated. This gives 0.73 g of methyl 6-methylthio-4-trifluoromethylpyridin-3-yicarboxylate; ¹H NMR (CDCl₃, ppm): 8.98, s, 1H; 7.48, S, 1H; 3.94, s, 3H; 2.64, s, 3H. Hydrolysis under the conditions mentioned above gives 6-methylthio-4-trifluoromethylnicotinic acid: ¹H NMR (CDCl₃, ppm): 9.02, s, 1H; 7.46, s, 1H; 2.64, s, 3H.

Example H5 6-Hydroxy-2-trifluoromethylpyridin-3-yl ethyl ester

[0229] Under an atmosphere of nitrogen and with stirring, 33.4 g of 3,4-dihydro-5-ethoxycarbonyl-6-trifluoromethylpyridin-2-one (Org. Res.& Devel. 1,370 (1997)) and 34 g of manganese dioxide in 250 ml of 1,2-dichlorobenzene are heated under reflux for 24 hours. In intervals of about 20 hours, manganese dioxide (total amount of MnO₂ used: 213 g) is added six more times over a period of 3 days, and the mixture is in each case heated further under ref lux. The mixture is then cooled, diluted with ethyl acetate, and filtered through silica gel, the filtercake is washed with ethyl ester and the filtrate is concentrated. The solid residue (26.7 g, i.e. 80%), which may still contain about 6% of starting material, is directly reacted further. For complete purification, it is possible to purify, for example, over silica gel (hexane/ethyl acetate 7:3) (¹H NMR, CDCl₃, ppm): 8.02 (d, 1H); 6.85 (d, 1H); 4.86 (q, 2H); 1.37 (t, 1H).

Example H6 Preparation of ethyl 6-chloro-2-trifluoromethyl pvridin-3-ylcarboxylate

[0230] In a bomb tube, 23.5 g of ethyl 6-hydroxy-2 4rifluoromethylpyridin-3-ylcarboxylate and 23.5 ml of phenyl dichlorophosphate are heated at 170° C. for 3 hours, and the mixture is, after cooling, added to ice-water, stirred for a few minutes and subsequently taken up in ethyl acetate and made slightly alkaline using sodium bicarbonate and then washed neutral with water. The extracts are admixed with a little hexane and filtered through silica gel. The filtrate is evaporated, leaving 21.6 g (85%) of the title compound in the form of a dark oil with n_(D) ³⁰, 1.4679. ¹H NMR (CDCl₃, ppm): 8.09 (d,1H); 7.60 (d,1 H); 4.43 (q, 2H); 1.43 (t,3H).

Example H7 Preparation of 6-chloro-2-trifluoromethylpyridin-3-ylcarboxylic acid

[0231] 2.5 g of the ethyl 6-chloro-2-trifluoromethylpyridin-3-ylcarboxylate obtained above are dissolved in the smallest possible amount of tetrahydrofuran, treated with approximately 20 g of ice and 11 ml of 1N lithium hydroxide and stirred at room temperature until hydrolysed completely. The mixture is then washed with a little ether and the aqueous phase is acidified using 4N hydrochloric acid and extracted with ethyl acetate. The extracts are washed with sodium chloride solution, dried and evaporated. This gives 1.8 g of the title compound of m.p. 154-156° C. The other free carboxylic acids are likewise obtained from their esters in this manner.

Example H8 Preparation of ethyl 6-methylthio-2-trifiuoromethylpyridin-3-ylcarboxylate

[0232] Under an atmosphere of nitrogen and with stirring, a solution of 1.7 g of 6-chloro-2-trifluoromethylpyridin-3-yl ethyl ester in 60 ml of dimethylformamide is treated a little at a time with 0.52 g of sodium methanethiolate and stirred at room temperature until the reaction has gone to completion. The reaction mixture is then poured into ice-water, made neutral by addition of a little dilute hydrochloric acid and extracted with ethyl acetate. The extracts are diluted with a little hexane, washed with water, dried over sodium sulfate, filtered and, after filtration through a little silica gel, evaporated. This gives 1.4 g (79%) of the title compound in the form of an oil with n_(D) ²⁵ 1.5100, ¹H NMR (CDCl₃, ppm): 7.90 (d, 1H); 7.40 (d, 1H); 1.40 (q, 2H); 2.60 (s, 3H); 1.49 (t, 3H).

Example H9 Preparation of ethyl 6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate

[0233] In an apparatus previously flushed with nitrogen, a solution of 1.8 ml of ethanethiol in 40 ml of dimethy lformamide, which had been cooled to 0° C., is treated a little at a time with 0.96 g of sodium hydride oil dispersion (60%), and the mixture is stirred at room temperature. After evolution of hydrogen has ceased, the mixture is cooled to −20° C., and a solution of 5.07 g of 6-chloro-2-trifluoromethylpyridin-3-yl ethyl ester in 10 ml of dimethylformamide is added dropwise at this temperature, and the mixture is stirred slowly until room temperature has been reached. After the reaction has ended (approximately 3 hours), the reaction mixture is added to ice-water and extracted with ethyl acetate. The extracts are washed with water, dried, filtered, evaporated and dried under high vacuum. This gives 5.0 g (89%) of the title compound as a brownish oil. ¹H NMR (CDCl₃, ppm): 7.90 (d, 1H); 7.35 (d, 1H); 4.40 (q, 2H); 3.25 (q, 2H); 1.38 (2t, 6H).

Example H10 Preparation of ethyl 6-ethylsulfinyl-2-trifluoromethylpyridin-3-ylcarboxylate

[0234] Under an atmosphere of nitrogen and with stirring and cooling, a solution of 2.5 g of m-chloroperbenzoic acid in 40 ml of methylene chloride is added dropwise at a temperature of −20° C. to a solution of 2.8 g of ethyl 6-ethylthio-2-trifluoromethylpyridin-3-ylcarboxylate, which had been charged initially, and the mixture is stirred at a temperature of +5° C. for 20 hours. The mixture is then evaporated gently and purified over silica gel (hexanelethyl acetate 7:3). This gives 2.48 g (84%) of 6-ethylsulfinyl-2-trifluoromethylpyridin-3-yl-ethyl ester. ¹H NMR (CDCl₃, ppm): 8.38 (d, 1H); 8.30 (d, 1H); 4.45 (q, 2H); 3.26-3.00 (m, 2H); 1.43 (t, 3H); 1.26 (t, 3H).

[0235] Ethyl 6-methylsulfinyl-2-trifluoromethylpyridin-3-ylcarboxylate is obtained in an analogous manner.

Example H11 Preparation of ethyl 6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate

[0236] Under an atmosphere of nitrogen and with stirring and cooling, 21 g of m-chloroperbenzoic acid are introduced a little at a time over a period of 30 minutes at a temperature of −20° C. into a solution of 3.6 g of 6-methylthio-2-trifluoromethylpyridin-3-yl ethyl ester, which had been charged initially, and the reaction mixture is stirred at room temperature for 5 hours. The mixture is then evaporated and filtered through silica gel (ethyl acetate/methanol/triethylamine 85:10:5). This gives 3.95 g (97%) of ethyl 6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate as a brownish solid with m.p. 70-72° C. ¹H NMR (CDCl₃, ppm): 8.40 (1H,d); 8.33 (1H,d); 4.47 (2H,q); 1.43 (3H,t).

Example H12 Preparation of ethyl 6-cyano-2-trifluoromethylpyridin-3-ylcarboxylate

[0237] Under an atmosphere of nitrogen and with stirring, a solution of 0.596 g of ethyl 6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate in 5 ml of dimethylformamide is treated with 160 mg of solid potassium cyanide and a spatula tipful of 1 8-crown-6, and the mixture is heated at 80° C. for 3 hours. The mixture is cooled overnight, and the next day another 30 mg of potassium cyanide are added and the mixture is heated further until the starting material has disappeared (approximately 2 hours). The mixture is then cooled, added to ice-water and extracted with ethyl acetate. The extracts are washed with water, dried, evaporated and freed from traces of dimethylformamide under high vacuum at approximately 40° C. This gives 480 mg (yield virtually quantitative) of ethyl 6-cyano-2-trifluoromethylpyridin-3-ylcarboxylate in the form of an oil which slowly solidifies. ¹H NMR (CDCl₃, ppm): 8.29 (1H,d); 7.97 (1H,d); 4.48 (2H, d); 1.43 (3H,t).

Example H13 Preparation of ethyl 6-methyl-2-trifluoromethylpyridin-3-ylcarboxylate

[0238] Under an atmosphere of nitrogen and with stirring, a solution of 3.6 g of 6-chloro-2-trifluoromethylpyridin-3-yl ethyl ester in 20 ml of dimethylacetamide is treated with 4.5 ml of tetramethyltin and 200 mg of dichloro(bistriphenylphosphine)palladium, and the mixture is heated to a temperature of 80-90° C. for 24 hours. Then another 1.5 ml of tetramethyltin and 30 mg of dichloro(bistriphenylphosphine)palladium are added and the mixture is heated for another 6 hours. The reaction mixture is then freed from excess tetramethyltin using reduced pressure (destruction by passing through ethanolic sodium hydroxide solution), cooled and added to ice-water. The mixture is extracted with diethyl ether and the extract is washed with water, dried over sodium sulfate, filtered through a little silica gel, evaporated and dried under reduced pressure. This gives the title compound (2.4 g, 73%), which still contains traces of dimethylacetamide, in the form of a dark oil. ¹H NMR (CDCl₃, ppm): 8.00 (1H,d); 7.42 (1H,d); 4.42 (2H, d); 2.68 (3H, s); 1.41 (3H,t). Hydrolysis analogously to the description already mentioned above affords 6-methyl-2-trifluoromethylpyridin-3-ylcarboxylic acid (brown resin) which is directly converted further into the carbonyl chloride.

Example H14 Preparation of 6-methyl-2-trifluoromethyl pvridin-3-ylcarbonyl chloride

[0239] A solution of 0.45 g of 6-methyl-2-trifluoromethylpyridin-3-ylcarboxyi ic acid in 20 ml of dichloromethane is charged initially, 3 drops of dimethylformamid c are added and the mixture is subsequently treated with 1.6 ml of oxalyl chloride. After the intensive evolution of gas has ceased, the mixture is kept at a bath temperature of 40° C. for another 1.5 hours and then evaporated. The crude product (0.56 g) that remains as residue can be directly reacted further. ¹H NMR (CDCl₃, ppm): 8.20 (1H,d); 7.51 (1H,d); 2.65 (3H, s).

Example H15 Preparation of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 6-methyl-2- trifluoromethylnicotinate

[0240] Under an atmosphere of nitrogen and with stirring and cooling, a solution of 0.56 g of 6-methyl-2-trifluoromethylpyridin-3-ylcarbonyl chloride in 10 ml of methylene chloride is added dropwise at 0° C. to a solution of 0.4 g of bicyclo[3.2.1]octane-2,4-dione and 0.72 g of triethylamine in 10 ml of methylene chloride, and the mixture is stirred for 5 hours until room temperature has been reached. The mixture is then diluted with methylene chloride, washed with cold 1N hydrochloric acid, dried and evaporated to give the desired enol ester (0 .8 9) as a brown resin which is directly reacted further. ¹H NMR (CDCl₃, ppm): 8.17 (1H,d); 7.51 (1H, d); 5.96 (1H, s); 3.04 (2H, m); 2.75 (3H, s);2.32-1.30 (m).

Example H16 Preparation of 4-hydroxy-3-(6-methyl-2-trifluoromethylpyridin-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

[0241] Under an atmosphere of nitrogen and with stirring, 0.8 g of the above enol ester is dissolved in 30 ml of acetonitrile at 25° C., and the mixture is treated with 0.5 ml of triethylamine and 0.4 ml of acetone cyanohydrin and stirred at room temperature for 20 hours. The mixture is then diluted with solvent and washed with dilute hydrochloric acid, dried and evaporated, and the residue is purified through a little silica gel (ethyl acetate/methanol/triethylamine 85:10:5). This gives 371 mg (46%) of the title compound (triethylamine salt) in the form of a yellowish resin. ¹H NMR (CDCl₃, ppm): 7.45 (1H, d); 7.25 (1H, d); 3.80-3.43 (4H, m); 3.18 (6H, m); 2.80 (2H, s(br)); 2.62 (3H, s); 220-1.54 (m).

Example H17 Preparation of ethyl 6-methoxy-2-trifluoromethylpyridin-3-ylcarboxylate

[0242] A suspension of 5.65 g of ethyl 6-hydroxy-2-trifluoromethylpyridin-3-ylcarboxylate, 6.0 g of potassium carbonate and 2.7 ml of methyl iodide is, together with a spatula tipful of 18-crown-6, heated to a temperature of 60-70° C. until the reaction has gone to completion. The mixture is then filtered, the filtration residue is washed with acetonitrile and the filtrate is concentrated under reduced pressure. The residue is cooled, admixed with ice-water, neutralized with dilute sulfuric acid and extracted with ethyl acetate. The extracts are washed with water, dried, diluted with a little hexane and filtered through a little silica gel.

[0243] The resulting residue is the title compound (3.7 g, 65%) in the form of slightly orange crystals of m.p. 150-152° C.

[0244]¹H NMR (CDCl₃, ppm): 8.00 (1H, d); 6.83 (1H, d); 4.38 (2H, q); 4.01 (3H, s);1.39 (3H, t).

Example H18 Preparation of 4-hydroxy-3(2-methyl-6-trifluoromethylpyridin-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

[0245] 6.68 g (0.0305 mol) of methyl 2-methyl-6-trifluoromethyinicotinate (prepared as described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanovwater (3:1 mixture), and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added a little at a time at 22° C. After 4 hours at 22° C, the reaction mixture is poured into ethyl acetate and 2N hydrochloric acid, the organic phase is washed three times with water, dried with sodium sulfate and evaporated and the residue is triturated with a little hexane. Filtration gives 5.69 9 (90% of theory) of the expected 2-methyl-6-trifluoromethyinicotinic acid of m.p. 147-149° C. The 2-methyl6trifluoromethyinicotinic acid obtained (2.0 g, 0.0098 mol) is dissolved in 20 ml of oxalyl chloride. Three drops of dimethylformamide are added, and the mixture is heated under reflux for 1 hour. The mixture is then concentrated using a rotary evaporator, and the residue (2-methyl-6-trifluoromethyinicotinoyl chloride) is taken up in 30 ml of methylene chloride. At I YC, 2.7 ml (0.0196 mo l) of triethylamine and 0.12 g (0.00098 mol) of dimethylaminopyridine are added. 1.49 g (0.0108 mol) of bicyclo[3.2.1]octane-2,4-dione, dissolved in 20 ml of methylene chloride, are then added dropwise. After 3 hours at 22° C., the reaction mixture is extracted with 2 N hydrochloric acid. The methylene chloride phase is separated off, washed with water and subsequently extracted with 10% aqueous sodium bicarbonate solution, dried over sodium sulfate and evaporated. This gives 3.18 g (100% of theory) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-6-trifluoromethyinicotinate as an oil, which can be processed further without purification.

[0246] 3.02 g (0.0093 mol) of 4-oxobicyclo [3.2.1]oct-2en-2-yl 2-methyl-6-trifluoromethyinicotinate and 1.9 ml (0.0136 mo l) of triethylamine are dissolved in 45 ml of acetonitrile. At 22° C., 0.01 ml of acetone cyanohydrin are added. After 18 hours at 22° C., the reaction mixture is poured into dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with brine, dried over sodium sulfate and evaporated, and the residue is dissolved in a little warm acetone. The product crystallizes on standing. Filtration gives 0.99 g (33% of theory) of the expected 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one as white crystals (m.p. 75-77° C.).

Example H19 Preparation of 3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl benzoate

[0247] At 0° C., a solution of 0.562 g (0.0004 mol) of benzoyl chloride in 1 ml of tetrahydrofuran is added to a solution of 1.14 g (0.0035 mol) of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one and 0.517 g (0.004 mol) of ethyidiisopropylamine in 15 ml of tetrahydrofuran. The reaction mixture is stirred at 25° C. for 2 hours, evaporated and purified over silica gel (hexane/ethyl acetate 1:1). This gives 0.9 g (60%) of the title compound in the form of a yellowish resin. ¹H NMR (CDCl₃, ppm): 7.91-7.87, m, 3H; 7.64, t, J=7.5 Hz, 1 H; 7.5 0-7.40, m, 3H; 3.24, br t, J=4 Hz, 1 H; 3.14, br t, J=4 Hz, 1H; 2.70, s, 3H; 2.47, d, J=13.5 Hz, 1H; 2.40, 2.15, m, 3H; 1.95-1.8, m, 2H.

Example H20 Preparation of 4-hydroxy-3-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

[0248] 16.25 g (0.05 mol) of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one and 9.4 g (0.1 mol) of urea/hydrogen peroxide complex are dissolved in 150 ml of methylene chloride, and 20.5 ml (0.15 mol) of trifluoroacetic anhydride are added dropwise at 25° C. After 14 hours at 25° C., the reaction mixture is added to ethyl acetate and water, and the organic phase is washed twice with water, dried with sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetatelmethanol 9/1). This gives 6.8 g (40%) of the desired product as white crystals (m.p. 109-110° C.).

Example H21 Preparation of 4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one

[0249] 20.15 g (0.062 mo l) of 4-hydroxy-3-(2-methyl-6-trifluoromethyipyridine-3carbonyl)-bicyclo[3.2.1]oct-3-en-2-one are suspended in 50 ml of oxalyl chloride, and 0.1 ml of dimethylformamide are added dropwise. After the intensive evolution of gas has ceased, the mixture is kept at a bath temperature of 45° C. for another 1.5 hours and then evaporated, and the residue is suspended in a little ethyl acetate and admixed with stirring at 0° C. with hexane. Filtration gives 19.19 g (90% of theory) of 4-chloro-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one of m.p. 137-138° C.

Example H22 Preparation of 4-amino-3-(2-methyl-6-trifluoronmethvlpvridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2one

[0250] 1.0 g (0.0029 mol) of 4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one are dissolved in 10 ml of tetrahydrofuran and, at 25° C., treated with 2.0 ml of aqueous ammonia (30%). After 0.5 hours at 25° C., the reaction mixture is added to ethyl acetate and water, the organic phase is washed twice with water, dried with sodium sulfate and evaporated and the residue is triturated with a little ethyl acetate. Filtration gives 0.81 g (86% of theory) of 4-amino-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3en-2-one in the form of white crystals (m.p. 262-263° C). ¹H NMR (CDCl₃, ppm): 10.62 br s 1H; 8.223 br s 1H; 7.41, d, J=8.1 Hz, 1H; 7.35, d, J=8.1 Hz, 1H; 3.03, br t, J=4.8 Hz, 1H; 2.70, br t, J=4.8 Hz, 1H; 2.41, s, 3H; 1.97-2.14, m, 3H; 1.77-1.812, m, 1H; 1.47-1.70, m, 2H.

Example H23 Preparation of 4-(4-chlorophenylsulfanyl)-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

[0251] 2.0 g (0.0058 mol) of 4-chloro-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-bicyclo[3.2.1]oct-3-en-2-one, 0.07 g of dimethylaminopyridine (0.00058 mol) and 1.61 ml of triethylamine are dissolved in 15 ml of methylene chloride. At 25° C., 0.092 g (0.0064 mol) of 4-chlorothiophenol are added. After 2 hours at 22° C., the reaction mixture is evaporated and purified over silica gel (hexane/ethyl acetate 2:1). Recrystallization (hexane/acetic acid at −25° C.) gives pure 4-(4-chlorophenylsulfanyl)-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one: m.p. 130-131 ° C.

Example H24 Preparation of 4-(4-chlorobenzenesulfonyl)-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

[0252] 0.6 g (0.00133 mol) of the 4-(4-chlorophenylsul tanyl)-3-(2-methyl-6trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one obtained above is dissolved in methylene chloride, and 0.9 ml of peracetic acid (39% in acetic acid, 0.0053 mol) are added dropwise at 25° C. After 5 hours at 25° C., the reaction mixture is added to ethyl acetate and water, the organic phase is washed with water, dried with sodium sulfate and evaporated and the residue is triturated with a little hexane. Filtration gives 0.56 g (84% of theory) of 4-(4-chlorobenzenesulfonyl)-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one in the form of white crystals (m.p.166-167° C.).

Example H25 Preparation of (5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanone and cyclopropyl-[3-methylsulfanyl-5-(2-methyl-6-trifluoromethylpyridin-3-yl)isoxazol4-yl)methanone

[0253] 14.8 g (0.080 mol) of tert-butyl 3-cyclopropyl-3-oxopropionic acid ester are dissolved in 25 ml of MeOH, and 1.93 g (0 .080 mol) of magnesium are added. With ice-bath cooling, 7 ml of carbon tetrachloride are added dropwise, and the reaction mixture is stirred at a temperature of 22° C. for one hour. After evaporation, the residue is suspended in 100 ml of acetonitrile, and 16.31 g (0.073 mol) of 2-methyl-6-trifluoromethyinicotinoyl chloride (prepared as described in Example H18), dissolved in 50 ml of acetonitrile, are added dropwise at a temperature of 22° C. After 6 hours, the reaction mixture is taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The ethyl acetate phase is separated off, washed with water, dried over sodium sulfate and evaporated. The residue is dissolved in 160 ml of methylene chloride, and 10 ml of trifluoroacetic acid are added dropwise at a temperature of 22° C. After 18 hours, the reaction mixture is poured into water and extracted with methylene chloride. The methylene chloride phase is washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. This gives 17.3 g (88% of theory) of 1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)propane-1,3-dione as an oil, which is processed further without purification. The 1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)propane-1,3-dione obtained above (15.0 g, 0.055 mol) is dissolved in 150 ml of dimethylformamide, and 50 g of potassium fluoride on an aluminium oxide support (alumina) (0.0055 movg, 0.276 mol) are added a little at a time at a temperature of 0° C. After 5 minutes, 6.7 g (0.088 mol) of carbon disulfide are added dropwise. After 2 hours, 23.6 g (0.166 mol) of methyl iodide are added dropwise, and the reaction mixture is warmed to a temperature of 22° C. After a further 2 hours, the alumina is filtered off, the filtrate is added to water and the mixture is extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane 15/1). This gives 12.0 g (60% of theory) of 2-(bismethylsulfanylmethylene)-1-cyclopropyl-3-(2-methyl-6-trifluoromethylpyridin-3-yl)-propane-1,3-dione as a solid. 12.0 g (0.033 mol) of the product obtained above are, together with 5.4 g (0.066 mol) of anhydrous sodium acetate, suspended in 120 ml of ethanol. 4.6 g (0.066 mol) of hydroxylamine hydrochloride are added, and the reaction mixture is kept at a temperature of 22° C. for 5 hours. Another 2.7 g of anhydrous sodium acetate and 2.3 g of hydroxylamine hydrochloride are then added. After 18 hours, the reaction mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate phase is washed with water and then with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. Trituration with a little ethyl acetate gives 9.0 g (79.5%) of the desired product as a 2:1 isomer mixture in the form of white crystals (m.p. 103-104° C.).

[0254] Main isomer: ¹H NMR (CDCl₃, ppm) ((5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanone) 7.98, d, J=7.8 Hz, 1H; 7.61, d, J=7.8 Hz, 1H; 2.67, s, 3H; 2.50, s, 3H; 2.02-1.93, m, 1 H; 1.34-1.28, m, 2H; 1.18-1.09, m, 2H.

[0255]¹H NMR (CDCl₃, ppm) (cyclopropyl-13-methylsulfanyl-5-(2-methy l -trifluoromethylpyridin-3-yl)isoxazol-4-yl]methane): 7.95, d, J=7.8 Hz, 1H; 7.69, d, J=7.8 Hz, 1H; 2.67, s, 3H; 2.66, s, 3H; 1.74-1.64, m, 1H; 1.28-1.18, m, 2H; 0.89 4.80, m, 2H.

Example H26 Preparation of (5-cyclopropyl-3-methylsulfinylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanone and cylopropyl-[3-methanesulfinyl-5-(2-methyl-6-trifluoromethylpyridin-3-yl)isoxazol-4-yl]methanone

[0256] 1.50 g (0.0043 mol) of the isomer mixture obtained above are dissolved in 30 ml of acetonelwater (2:1 mixture), and 1.02 g (0.0048 mol) of sodium metaperiodate are added a little at a time at 22° C. After 5 hours, the reaction mixture is evaporated using a rotary evaporator. The residue is taken up in water and ethyl acetate. The ethyl acetate phase is dried over sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane 3/1). This gives initially 0.8 g (51 % of theory) of (5-cyclopropyl-3-methylsulfinylisoxazol-4-yl)-(2-methyl-6-trifluoromethylpyridin-3-yl)methanone as white crystals (m.p. 96-97° C.). ¹H NMR (CDCl₃, ppm): 7.86, d, J=7.8 Hz, 1H; 7.59, d, J=7.8 Hz, 1H; 3.078, s, 3H; 2.66, s, 3H; 1.54-1A49, m, IH; 1.32-1.25, m, 2H; 1.13-1.072, m, 2H.

[0257] The second product that eiutes consists of 0.34 g (22% of theory) of cyclopropyl-[3-methanesulfinyl-5-(2-methyl-6-trifluoromethylpyridin-3yl)isoxazol4-yl]methanone as white crystals (m.p. 112-113° C.). ¹H NMR (CDCl₃, ppm): 7.97, d, J=7.8 Hz, 1H; 7.67, d, J=7.8 Hz, 1H; 3.128, s, 3H; 2.62, s, 3H; 1.69-1.64, m, 1H; 1.26-1.18, m, 2H; 0.90-0.85, m, 2H.

Example H27 Preparation of (5-cyclopropyl-3-methanesulfonylisoxazol-4-yl)-(2-isopropyl-6-trifluoromethylpyridin-3-yl)methanone

[0258] 0.15 g (0.0045 mol) of (5-cyclopropyl-3-methylsulfanylisoxazol-4-yl)-(2-isopropyl-6-trifluoromethylpyridin-3-yl)methanone is dissolved in methylene chloride, and 0.28 ml of peracetic acid (39% in acetic acid, 0.0016 mol) are added dropwise at a temperature of 5° C. After 15 hours at 25° C., the reaction mixture is added to ethyl acetate and water, and the organic phase is washed with water, dried with sodium sulfate and evaporated. The residue is chromatographed over silica gel (mobile phase: ethyl acetate/hexane 5/1). This gives 0.121 g (74% of theory) of the expected product as white crystals (m.p.105-106° C.).

[0259] In an analogous manner, and according to the methods shown in the general reaction schemes 1-10 and in the references mentioned therein, it is also possible to prepare the compounds listed in the tables below. In these tables, CCH is the ethynyl group, Ph is the phenyl group and Me is the methyl group. TABLE 1

Comp. No. R₁ R₂ R₃ R₄ R₅ p 1.001 H CF₃ H H OH 0 1.002 F CF₃ H H OH 0 1.003 Cl CF₃ H H OH 0 1.004 Br CF₃ H H OH 0 1.005 CHF₂ CF₃ H H OH 0 1.006 CCl₃ CF₃ H H OH 0 1.007 CClF₂ CF₃ H H OH 0 1.008 CF₃ CF₃ H H OH 0 1.009 CH₃ CF₃ H H OH 0 1.01 CH₂CH₃ CF₃ H H OH 0 1.011 CH(CH₃)₂ CF₃ H H OH 0 1.012 (CH₂)₂CH₃ CF₃ H H OH 0 1.013 C(CH₃)₃ CF₃ H H OH 0 1.014 Ph CF₃ H H OH 0 1.015 CH₂F CF₃ H H OH 0 1.016 CH₂Cl CF₃ H H OH 0 1.017 CH₂Br CF₃ H H OH 0 1.018 CH₂OH CF₃ H H OH 0 1.019 CH₂OCOCH₃ CF₃ H H OH 0 1.02 CH₂OCOPh CF₃ H H OH 0 1.021 CH₂OCH₃ CF₃ H H OH 0 1.022 CH₂OCH₂CH₃ CF₃ H H OH 0 1.023 CH₂CH₂OCH₃ CF₃ H H OH 0 1.024 CH₂SMe CF₃ H H OH 0 1.025 CH₂SOMe CF₃ H H OH 0 1.026 CH₂SO₂Me CF₃ H H OH 0 1.027 CH₂SO₂Ph CF₃ H H OH 0 1.028 SCH₂Ph CF₃ H H OH 0 1.029 SOCH₂Ph CF₃ H H OH 0 1.03 SO₂CH₂Ph CF₃ H H OH 0 1.031 SCH₃ CF₃ H H OH 0 1.032 SOCH₃ CF₃ H H OH 0 1.033 SO₂CH₃ CF₃ H H OH 0 1.034 SPh CF₃ H H OH 0 1.035 SOPh CF₃ H H OH 0 1.036 SO₂Ph CF₃ H H OH 0 1.037 N(CH₃)₂ CF₃ H H OH 0 1.038 CH═CH₂ CF₃ H H OH 0 1.039 CH₂CH═CH₂ CF₃ H H OH 0 1.04 SO₂N(CH₃)₂ CF₃ H H OH 0 1.041 ethynyl CF₃ H H OH 0 1.042 cyclopropyl CF₃ H H OH 0 1.043 OCH₃ CF₃ H H OH 0 1.044 OPh CF₃ H H OH 0 1.045 OCHF₂ CF₃ H H OH 0 1.046 CO₂Me CF₃ H H OH 0 1.047 2-furyl CF₃ H H OH 0 1.048 OCH₂ethynyl CF₃ H H OH 0 1.049 2-pyridyl CF₃ H H OH 0 1.05 3-pyridyl CF₃ H H OH 0 1.051 4-pyridyl CF₃ H H OH 0 1.052 H CF₃ H H OH 1 1.053 F CF₃ H H OH 1 1.054 Cl CF₃ H H OH 1 1.055 Br CF₃ H H OH 1 1.056 CHF₂ CF₃ H H OH 1 1.057 CCl₃ CF₃ H H OH 1 1.058 CClF₂ CF₃ H H OH 1 1.059 CF₃ CF₃ H H OH 1 1.06 CH₃ CF₃ H H OH 1 1.061 CH₂CH₃ CF₃ H H OH 1 1.062 CH(CH₃)₂ CF₃ H H OH 1 1.063 (CH₂)₂CH₃ CF₃ H H OH 1 1.064 C(CH₃)₃ CF₃ H H OH 1 1.065 Ph CF₃ H H OH 1 1.066 CH₂F CF₃ H H OH 1 1.067 CH₂Cl CF₃ H H OH 1 1.068 CH₂Br CF₃ H H OH 1 1.069 CH₂OH CF₃ H H OH 1 1.07 CH₂OCOCH₃ CF₃ H H OH 1 1.071 CH₂OCOPh CF₃ H H OH 1 1.072 CH₂OCH₃ CF₃ H H OH 1 1.073 CH₂OCH₂CH₃ CF₃ H H OH 1 1.074 CH₂CH₂OCH₃ CF₃ H H OH 1 1.075 CH₂SMe CF₃ H H OH 1 1.076 CH₂SOMe CF₃ H H OH 1 1.077 CH₂SO₂Me CF₃ H H OH 1 1.078 CH₂SO₂Ph CF₃ H H OH 1 1.079 SCH₂Ph CF₃ H H OH 1 1.08 SOCH₂Ph CF₃ H H OH 1 1.081 SO₂CH₂Ph CF₃ H H OH 1 1.082 SCH₃ CF₃ H H OH 1 1.083 SOCH₃ CF₃ H H OH 1 1.084 SO₂CH₃ CF₃ H H OH 1 1.085 SPh CF₃ H H OH 1 1.086 SOPh CF₃ H H OH 1 1.087 SO₂Ph CF₃ H H OH 1 1.088 N(CH₃)₂ CF₃ H H OH 1 1.089 CH═CH₂ CF₃ H H OH 1 1.09 CH₂CH═CH₂ CF₃ H H OH 1 1.091 SO₂N(CH₃)₂ CF₃ H H OH 1 1.092 ethynyl CF₃ H H OH 1 1.093 cyclopropyl CF₃ H H OH 1 1.094 OCH₃ CF₃ H H OH 1 1.095 OPh CF₃ H H OH 1 1.096 OCHF₂ CF₃ H H OH 1 1.097 CO₂Me CF₃ H H OH 1 1.098 2-furyl CF₃ H H OH 1 1.099 OCH₂CCH CF₃ H H OH 1 1.1 2-pyridyl CF₃ H H OH 1 1.101 3-pyridyl CF₃ H H OH 1 1.102 4-pyridyl CF₃ H H OH 1 1.103 H CF₂CF₃ H H OH 0 1.104 Cl CF₂CF₃ H H OH 0 1.105 CHF₂ CF₂CF₃ H H OH 0 1.106 CCl₃ CF₂CF₃ H H OH 0 1.107 CClF₂ CF₂CF₃ H H OH 0 1.108 CF₃ CF₂CF₃ H H OH 0 1.109 CH₃ CF₂CF₃ H H OH 0 1.11 CH₂CH₃ CF₂CF₃ H H OH 0 1.111 CH(CH₃)₂ CF₂CF₃ H H OH 0 1.112 (CH₂)₂CH₃ CF₂CF₃ H H OH 0 1.113 C(CH₃₎ ₃ CF₂CF₃ H H OH 0 1.114 CH₂F CF₂CF₃ H H OH 0 1.115 CH₂Cl CF₂CF₃ H H OH 0 1.116 CH₂OH CF₂CF₃ H H OH 0 1.117 CH₂OCOCH₃ CF₂CF₃ H H OH 0 1.118 CH₂OCOPh CF₂CF₃ H H OH 0 1.119 CH₂OCH₃ CF₂CF₃ H H OH 0 1.12 CH₂OCH₂CH₃ CF₂CF₃ H H OH 0 1.121 CH₂SMe CF₂CF₃ H H OH 0 1.122 CH₂SOMe CF₂CF₃ H H OH 0 1.123 CH₂SO₂Me CF₂CF₃ H H OH 0 1.124 CH₂SO₂Ph CF₂CF₃ H H OH 0 1.125 N(CH₃)₂ CF₂CF₃ H H OH 0 1.126 CH═CH₂ CF₂CF₃ H H OH 0 1.127 CH₂CH═CH₂ CF₂CF₃ H H OH 0 1.128 SO₂N(CH₃)₂ CF₂CF₃ H H OH 0 1.129 CCH CF₂CF₃ H H OH 0 1.13 cyclopropyl CF₂CF₃ H H OH 0 1.131 OPh CF₂CF₃ H H OH 0 1.132 OCH₃ CF₂CF₃ H H OH 0 1.133 CO₂Me CF₂CF₃ H H OH 0 1.134 OCH₂CCH CF₂CF₃ H H OH 0 1.135 2-pyridyl CF₂CF₃ H H OH 0 1.136 3-pyridyl CF₂CF₃ H H OH 0 1.137 4-pyridyl CF₂CF₃ H H OH 0 1.138 H CF₂CF₃ H H OH 1 1.139 Cl CF₂CF₃ H H OH 1 1.14 CHF₂ CF₂CF₃ H H OH 1 1.141 CCl₃ CF₂CF₃ H H OH 1 1.142 CClF₂ CF₂CF₃ H H OH 1 1.143 CF₃ CF₂CF₃ H H OH 1 1.144 CH₃ CF₂CF₃ H H OH 1 1.145 CH₂CH₃ CF₂CF₃ H H OH 1 1.146 CH(CH₃)₂ CF₂CF₃ H H OH 1 1.147 (CH₂)₂CH₃ CF₂CF₃ H H OH 1 1.148 C(CH₃)₃ CF₂CF₃ H H OH 1 1.149 CH₂F CF₂CF₃ H H OH 1 1.15 CH₂Cl CF₂CF₃ H H OH 1 1.151 CH₂OH CF₂CF₃ H H OH 1 1.152 CH₂OCOCH₃ CF₂CF₃ H H OH 1 1.153 CH₂OCOPh CF₂CF₃ H H OH 1 1.154 CH₂OCH₃ CF₂CF₃ H H OH 1 1.155 CH₂OCH₂CH₃ CF₂CF₃ H H OH 1 1.156 CH₂SMe CF₂CF₃ H H OH 1 1.157 CH₂SOMe CF₂CF₃ H H OH 1 1.158 CH₂SO₂Me CF₂CF₃ H H OH 1 1.159 CH₂SO₂Ph CF₂CF₃ H H OH 1 1.16 N(CH₃)₂ CF₂CF₃ H H OH 1 1.161 CH═CH₂ CF₂CF₃ H H OH 1 1.162 CH₂CH═CH₂ CF₂CF₃ H H OH 1 1.163 SO₂N(CH₃)₂ CF₂CF₃ H H OH 1 1.164 CCH CF₂CF₃ H H OH 1 1.165 cyclopropyl CF₂CF₃ H H OH 1 1.166 OPh CF₂CF₃ H H OH 1 1.167 OCH₃ CF₂CF₃ H H OH 1 1.168 CO₂Me CF₂CF₃ H H OH 1 1.169 OCH₂CCH CF₂CF₃ H H OH 1 1.17 2-pyridyl CF₂CF₃ H H OH 1 1.171 3-pyridyl CF₂CF₃ H H OH 1 1.172 4-pyridyl CF₂CF₃ H H OH 1 1.173 H CF₂CF₂CF₃ H H OH 0 1.174 CHF₂ CF₂CF₂CF₃ H H OH 0 1.175 CF₃ CF₂CF₂CF₃ H H OH 0 1.176 CH₃ CF₂CF₂CF₃ H H OH 0 1.177 CH₂CH₃ CF₂CF₂CF₃ H H OH 0 1.178 (CH₂)₂CH₃ CF₂CF₂CF₃ H H OH 0 1.179 CH₂Cl CF₂CF₂CF₃ H H OH 0 1.18 CH₂OCH₃ CF₂CF₂CF₃ H H OH 0 1.181 H CF₂CF₂CF₃ H H OH 1 1.182 CHF₂ CF₂CF₂CF₃ H H OH 1 1.183 CF₃ CF₂CF₂CF₃ H H OH 1 1.184 CH₃ CF₂CF₂CF₃ H H OH 1 1.185 CH₂CH₃ CF₂CF₂CF₃ H H OH 1 1.186 (CH₂)₂CH₃ CF₂CF₂CF₃ H H OH 0 1.187 CH₂Cl CF₂CF₂CF₃ H H OH 1 1.188 CH₂OCH₃ CF₂CF₂CF₃ H H OH 1 1.189 H CF₂Cl H H OH 0 1.19 Cl CF₂Cl H H OH 0 1.191 CHF₂ CF₂Cl H H OH 0 1.192 CCl₃ CF₂Cl H H OH 0 1.193 CClF₂ CF₂Cl H H OH 0 1.194 CF₃ CF₂Cl H H OH 0 1.195 CH₃ CF₂Cl H H OH 0 1.196 CH₂CH₃ CF₂Cl H H OH 0 1.197 CH(CH₃)₂ CF₂Cl H H OH 0 1.198 (CH₂)₂CH₃ CF₂Cl H H OH 0 1.199 C(CH₃₎ ₃ CF₂Cl H H OH 0 1.2 CH₂F CF₂Cl H H OH 0 1.201 CH₂Cl CF₂Cl H H OH 0 1.202 CH₂OH CF₂Cl H H OH 0 1.203 CH₂OCOCH₃ CF₂Cl H H OH 0 1.204 CH₂OCOPh CF₂Cl H H OH 0 1.205 CH₂OCH₃ CF₂Cl H H OH 0 1.206 CH₂OCH₂CH₃ CF₂Cl H H OH 0 1.207 CH₂SMe CF₂Cl H H OH 0 1.208 CH₂SOMe CF₂Cl H H OH 0 1.209 CH₂SO₂Me CF₂Cl H H OH 0 1.21 CH₂SO₂Ph CF₂C H H OH 0 1.211 N(CH₃)₂ CF₂Cl H H OH 0 1.212 CH═CH₂ CF₂Cl H H OH 0 1.213 CH₂CH═CH₂ CF₂Cl H H OH 0 1.214 SO₂N(CH₃)₂ CF₂Cl H H OH 0 1.215 CCH CF₂Cl H H OH 0 1.216 cyclopropyl CF₂Cl H H OH 0 1.217 OPh CF₂Cl H H OH 0 1.218 OCH₃ CF₂Cl H H OH 0 1.219 CO₂Me CF₂Cl H H OH 0 1.22 OCH₂CCH CF₂Cl H H OH 0 1.221 2-pyridyl CF₂Cl H H OH 0 1.222 3-pyridyl CF₂Cl H H OH 0 1.223 4-pyridyl CF₂Cl H H OH 0 1.224 H CF₂Cl H H OH 1 1.225 Cl CF₂Cl H H OH 1 1.226 CHF₂ CF₂Cl H H OH 1 1.227 CCl₃ CF₂Cl H H OH 1 1.228 CClF₂ CF₂Cl H H OH 1 1.229 CF₃ CF₂Cl H H OH 1 1.23 CH₃ CF₂Cl H H OH 1 1.231 CH₂CH₃ CF₂Cl H H OH 1 1.232 CH(CH₃)₂ CF₂Cl H H OH 1 1.233 (CH₂)₂CH₃ CF₂Cl H H OH 1 1.234 C(CH₃₎ ₃ CF₂Cl H H OH 1 1.235 CH₂F CF₂Cl H H OH 1 1.236 CH₂Cl CF₂Cl H H OH 1 1.237 CH₂OH CF₂Cl H H OH 1 1.238 CH₂OCOCH₃ CF₂Cl H H OH 1 1.239 CH₂OCOPh CF₂Cl H H OH 1 1.24 CH₂OCH₃ CF₂Cl H H OH 1 1.241 CH₂OCH₂CH₃ CF₂Cl H H OH 1 1.242 CH₂SMe CF₂Cl H H OH 1 1.243 CH₂SOMe CF₂Cl H H OH 1 1.244 CH₂SO₂Me CF₂Cl H H OH 1 1.245 CH₂SO₂Ph CF₂Cl H H OH 1 1.246 N(CH₃)₂ CF₂Cl H H OH 1 1.247 CH═CH₂ CF₂Cl H H OH 1 1.248 CH₂CH═CH₂ CF₂Cl H H OH 1 1.249 SO₂N(CH₃)₂ CF₂Cl H H OH 1 1.25 CCH CF₂Cl H H OH 1 1.251 cyclopropyl CF₂Cl H H OH 1 1.252 OPh CF₂Cl H H OH 1 1.253 OCH₃ CF₂Cl H H OH 1 1.254 CO₂Me CF₂Cl H H OH 1 1.255 OCH₂CCH CF₂Cl H H OH 1 1.256 H CCl₃ H H OH 0 1.257 Cl CCl₃ H H OH 0 1.258 CH₃ CCl₃ H H OH 0 1.259 CH₂CH₃ CCl₃ H H OH 0 1.26 CH(CH₃)₂ CCl₃ H H OH 0 1.261 (CH₂)₂CH₃ CCl₃ H H OH 0 1.262 CH₂F CCl₃ H H OH 0 1.263 CH₂Cl CCl₃ H H OH 0 1.264 CH₂OH CCl₃ H H OH 0 1.265 CH₂OCOCH₃ CCl₃ H H OH 0 1.266 CH₂OCOPh CCl₃ H H OH 0 1.267 CH₂OCH₃ CCl₃ H H OH 0 1.268 CH₂OCH₂CH₃ CCl₃ H H OH 0 1.269 CH₂SMe CCl₃ H H OH 0 1.27 CH₂SOMe CCl₃ H H OH 0 1.271 CH₂SO₂Me CCl₃ H H OH 0 1.272 CH₂SO₂Ph CCl₃ H H OH 0 1.273 cyclopropyl CCl₃ H H OH 0 1.274 OPh CCl₃ H H OH 0 1.275 OCH₃ CCl₃ H H OH 0 1.276 CO₂Me CCl₃ H H OH 0 1.277 OCH₂OCH CCl₃ H H OH 0 1.278 H CCl₃ H H OH 1 1.279 Cl CCl₃ H H OH 1 1.28 CH₃ CCl₃ H H OH 1 1.281 CH₂CH₃ CCl₃ H H OH 1 1.282 CH(CH₃)₂ CCl₃ H H OH 1 1.283 (CH₂)₂CH₃ CCl₃ H H OH 1 1.284 CH₂F CCl₃ H H OH 1 1.285 CH₂Cl CCl₃ H H OH 1 1.286 CH₂OH CCl₃ H H OH 1 1.287 CH₂OCOCH₃ CCl₃ H H OH 1 1.288 CH₂OCOPh CCl₃ H H OH 1 1.289 CH₂OCH₃ CCl₃ H H OH 1 1.29 CH₂OCH₂CH₃ CCl₃ H H OH 1 1.291 CH₂SMe CCl₃ H H OH 1 1.292 CH₂SOMe CCl₃ H H OH 1 1.293 CH₂SO₂Me CCl₃ H H OH 1 1.294 CH₂SO₂Ph CCl₃ H H OH 1 1.295 cyclopropyl CCl₃ H H OH 1 1.296 OPh CCl₃ H H OH 1 1.297 OCH₃ CCl₃ H H OH 1 1.298 CO₂Me CCl₃ H H OH 1 1.299 OCH₂CCH CCl₃ H H OH 1 1.3 CF₃ CHF₂ H H OH 0 1.301 CH₃ CHF₂ H H OH 0 1.302 CH₂OCH₃ CHF₂ H H OH 0 1.303 CH₂Cl CHF₂ H H OH 0 1.304 CH₂F CHF₂ H H OH 0 1.305 CF₃ CHF₂ H H OH 1 1.306 CH₃ CHF₂ H H OH 1 1.307 CH₂OCH₃ CHF₂ H H OH 1 1.308 CH₂Cl CHF₂ H H OH 1 1.309 CH₂F CHF₂ H H OH 1 1.31 CH₃ CF₃ H CH₃ OH 0 1.311 CH₃ CF₃ H CH₃ OH 1 1.312 Cl CF₃ H CH₃ OH 0 1.313 CH₃ CF₃ CH₃ H OH 0 1.314 CH₃ CF₃ Ph H OH 0 1.315 CH₃ CF₃ Cl H OH 0 1.316 CH₃ CF₃ CO₂CH₂CH₃ H OH 0 1.317 CH₃ CF₃ CO₂CH₂Ph H OH 0 1.318 CH₃ CF₃ CH₃ H OH 1 1.319 CH₃ CF₃ Ph H OH 1 1.32 CH₃ CF₃ Cl H OH 1 1.321 CH₃ CF₃ CO₂CH₂CH₃ H OH 1 1.322 CH₃ CF₃ CO₂CH₂Ph H OH 1 1.323 OCH₃ CF₃ CH₃ H OH 0 1.324 CH₂OCH₃ CF₃ CH₃ H OH 0 1.325 CH₂OCH₃ CF₃ Ph H OH 0 1.326 CH₂OCH₃ CF₃ Cl H OH 0 1.327 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 0 1.328 CH₂OCH₃ CF₃ CO₂CH₂Ph H OH 0 1.329 CH₂OCH₃ CF₃ CH₃ H OH 1 1.33 CH₂OCH₃ CF₃ Ph H OH 1 1.331 CH₂OCH₃ CF₃ Cl H OH 1 1.332 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 1 1.333 CH₂OCH₃ CF₃ CO₂CH₂Ph H OH 1 1.334 COOCH₃ H H H OH 0 1.335 CF₃ SCH₃ H H OH 0 1.336 CH₃ SCH₃ H H OH 0 1.337 CF₃ SOCH₃ H H OH 0 1.338 CH₃ SOCH₃ H H OH 0 1.339 CF₃ SO₂CH₃ H H OH 0 1.34 CH₃ SO₂CH₃ H H OH 0 1.341 CF₃ SCH₂CH₃ H H OH 0 1.342 CH₃ SCH₂CH₃ H H OH 0 1.343 CF₃ SOCH₂CH₃ H H OH 0 1.344 CH₃ SOCH₂CH₃ H H OH 0 1.345 CF₃ SO₂CH₂CH₃ H H OH 0 1.346 CH₃ SO₂CH₂CH₃ H H OH 0 1.347 CF₃ OCH₃ H H OH 0 1.348 CH₃ OCH₃ H H OH 0 1.349 CF₃ OCH₂CF₃ H H OH 0 1.35 CH₃ OCH₂CF₃ H H OH 0 1.351 CF₃ OCH₂CCH H H OH 0 1.352 CH₃ OCH₂CCH H H OH 0 1.353 CF₃ CN H H OH 0 1.354 CH₃ CN H H OH 0 1.355 CF₃ Cl H H OH 0 1.356 CF₃ Cl H H O-NEt₃+ 0 1.357 CH₃ Cl H H OH 0 1.358 H Cl H H OH 0 1.359 CF₃ OCH₃ H H OH 0 1.36 CH₃ OCH₃ H H OH 0 1.361 CF₃ CH₃ H H OH 0 1.362 H CF₃ H CH₃ OH 0 1.363 H CF₃ H CF₃ OH 0 1.364 H CF₃ H CH₂CH₃ OH 0 1.365 H CF₃ H CF₃ OH 0 1.366 H CF₃ H SCH₃ OH 0 1.367 H CF₃ H SOCH₃ OH 0 1.368 H CF₃ H SO₂CH₃ OH 0 1.369 H CF₃ H Cl OH 0 1.37 H CF₃ H OCH₃ OH 0 1.371 H CH₃ H CF₃ OH 0 1.372 H Cl H CF₃ OH 0 1.373 H OCH₃ H CF₃ OH 0 1.374 H SCH₃ H CF₃ OH 0 1.375 H SOCH₃ H CF₃ OH 0 1.376 CH₃ CF₃ H H O-K+ 0 1.377 CH₃ CF₃ H H S(CH₂)₇CH₃ 0 1.378 CH₃ CF₃ H H S(CH₂)₇CH₃ 0 1.379 CH₃ CF₃ H H SO(CH₂)₇CH₃ 0 1.38 CH₃ CF₃ H H SO₂(CH₂)₇CH₃ 0 1.381 CH₃ CF₃ H H SPh 0 1.382 CH₃ CF₃ H H SOPh 0 1.383 CH₃ CF₃ H H SO₂Ph 0 1.384 CH₃ CF₃ H H NOCH₃ 0 1.385 CH₃ CF₃ H H NOCH₂Ph 0 1.386 CH₃ CF₃ H H NOCH₂CH═CH₂ 0 1.387 CH₃ CF₃ H H NOC(CH₃)₃ 0 1.388 CH₃ CF₃ H H NOCH₂CH₃ 0 1.389 CH₃ CF₃ H H NCH₂CH₂SH 0 1.39 CH₃ CF₃ H H NN(CH₃)₂ 0 1.391 CH₃ CF₃ H H NN(CH₃)C(S)NH₂ 0 1.392 CH₃ CF₃ H H N-morpholino 0 1.393 CH₃ CF₃ H H NHCOCH₃ 0 1.394 CH₃ CF₃ H H NHCO(CH₂)₇CH₃ 0 1.395 CH₃ CF₃ H H NHCOPh 0 1.396 CH₃ CF₃ H H NHSO₂CH₃ 0 1.397 CH₃ CF₃ H H NH(CO)S(CH₂)₇CH₃ 0 1.398 CH₃ CF₃ H H Cl 0 1.399 CH₃ CF₃ H H NH₂ 0 1.4 CH₃ CF₃ H H OCOC(CH₃)₃ 0 1.401 CH₃ CF₃ H H OCOCH₃ 0 1.402 CH₃ CF₃ H H OCOPh 0 1.403 CH₃ CF₃ H H OCO-cyclopropyl 0 1.404 CH₃ CF₃ H H OCOCH₂CH₃ 0 1.405 CH₃ CF₃ H H OCOCH═CH₂ 0 1.406 CH₃ CF₃ H H OCOCH═CHCH₃ 0 1.407 CH₃ CF₃ H H O(CO)SCH₃ 0 1.408 CH₃ CF₃ H H O(CO)S(CH₂)₇CH₃ 0 1.409 CH₃ CF₃ H H O(CO)OCH₂CH₃ 0 1.41 CH₃ CF₃ H H O(CO)N(CH₂CH₃)₂ 0 1.411 CH₃ (CF₂)₃CF₃ H H OH 0 1.412 CH₃ CF₃ H H S-(4-Cl-phenyl) 0 1.413 CH₃ CF₃ H H SO-(4-Cl-phenyl) 0 1.414 CH₃ CF₃ H H SO₂-(4-Cl-phenyl) 0 1.415 CH₃ CF₃ H H S-(4-CF₃-phenyl) 0 1.416 CH₃ CF₃ H H SO-(4-CF₃-phenyl) 0 1.417 CH₃ CF₃ H H SO₂-(4-CF₃-phenyl) 0 1.418 CH₃ CF₃ H H S-(4-NO₂-phenyl) 0 1.419 CH₃ CF₃ H H SO-(4-NO₂-phenyl) 0 1.42 CH₃ CF₃ H H SO₂-(4-NO₂-phenyl) 0 1.421 CH₃ CF₃ H H

0 1.422 CH₃ CF₃ H H

0 1.423 CH₃ CF₃ H H

0 1.424 CH₃ CF₃ H H

0 1.425 CF₂H SCH₃ H H OH 0 1.426 CF₂Cl SCH₃ H H OH 0 1.427 CF₂H SOCH₃ H H OH 0 1.428 CF₂Cl SOCH₃ H H OH 0 1.429 CF₂H SO₂CH₃ H H OH 0 1.43 CF₂Cl SO₂CH₃ H H OH 0 1.431 CF₂H SCH₂CH₃ H H OH 0 1.432 CF₂Cl SCH₂CH₃ H H OH 0 1.433 CF₂H SOCH₂CH₃ H H OH 0 1.434 CF₂Cl SOCH₂CH₃ H H OH 0 1.435 CF₂H SO₂CH₂CH₃ H H OH 0 1.436 CF₂Cl SO₂CH₂CH₃ H H OH 0 1.437 CF₂H OCH₃ H H OH 0 1.438 CF₂Cl OCH₃ H H OH 0 1.439 CF₂H OCH₂CF₃ H H OH 0 1.44 CF₂Cl OCH₂CF₃ H H OH 0 1.441 CF₂H OCH₂CCH H H OH 0 1.442 CF₂Cl OCH₂CCH H H OH 0 1.443 CF₂H CN H H OH 0 1.444 CF₂Cl CN H H OH 0 1.445 CF₂H Cl H H OH 0 1.446 CF₂Cl Cl H H OH 0 1.447 CF₂H OCH₃ H H OH 0 1.448 CF₂Cl OCH₃ H H OH 0 1.449 CF₃ CH₂OCH₃ H H OH 0 1.45 CF₃ CH₂OCH₃ H H OH 1 1.451 CF₂Cl CH₂OCH₃ H H OH 0 1.452 CF₂Cl CH₂OCH₃ H H OH 1 1.453 CF₂H CH₂OCH₃ H H OH 0 1.454 CF₂H CH₂OCH₃ H H OH 1 1.455 CN CF₃ H H OH 0

[0260] TABLE 2

Comp. No. R₁ R₂ R₃ R₄ 2.001 H CF₃ H H 2.002 F CF₃ H H 2.003 Cl CF₃ H H 2.004 Br CF₃ H H 2.005 CHF₂ CF₃ H H 2.006 CCl₃ CF₃ H H 2.007 CClF₂ CF₃ H H 2.008 CF₃ CF₃ H H 2.009 CH₃ CF₃ H H 2.01 CH₂CH₃ CF₃ H H 2.011 CH(CH₃)₂ CF₃ H H 2.012 (CH₂)₂CH₃ CF₃ H H 2.013 Ph CF₃ H H 2.014 CH₂F CF₃ H H 2.015 CH₂Cl CF₃ H H 2.016 CH₂Br CF₃ H H 2.017 CH₂OH CF₃ H H 2.018 CH₂OCOCH₃ CF₃ H H 2.019 CH₂OCOPh CF₃ H H 2.02 CH₂OCH₃ CF₃ H H 2.021 CH₂OCH₂CH₃ CF₃ H H 2.022 CH₂CH₂OCH₃ CF₃ H H 2.023 CH₂SMe CF₃ H H 2.024 CH₂SOMe CF₃ H H 2.025 CH₂SO₂Me CF₃ H H 2.026 CH₂SO₂Ph CF₃ H H 2.027 SCH₂ph CF₃ H H 2.028 SOCH₂Ph CF₃ H H 2.029 SO₂CH₂Ph CF₃ H H 2.03 SCH₃ CF₃ H H 2.031 SOCH₃ CF₃ H H 2.032 SO₂CH₃ CF₃ H H 2.033 N(CH₃)₂ CF₃ H H 2.034 CH═CH₂ CF₃ H H 2.035 CH₂CH═CH₂ CF₃ H H 2.036 SO₂N(CH₃)₂ CF₃ H H 2.037 CCH CF₃ H H 2.038 OCH₃ CF₃ H H 2.039 OPh CF₃ H H 2.04 OCHF₂ CF₃ H H 2.041 CO₂Me CF₃ H H 2.042 OCH₂CCH CF₃ H H 2.043 OCH₂CF₃ CF₃ H H 2.044 H CF₃ H Cl 2.045

F H Cl 2.046 CN CF₃ H H 2.047 H CHF₂ H H 2.048 CH₃ CHF₂ H H 2.049 CH₂CH₃ CHF₂ H H 2.05 CH₂OCH₃ CHF₂ H H 2.051 H CF₂Cl H H 2.052 CH₃ CF₂Cl H H 2.053 CH₂CH₃ CF₂Cl H H 2.054 CH₂OCH₃ CF₂Cl H H

[0261] TABLE 3

Comp. No. R₁ R₂ R₃ R₄ 3.001 H CF₃ H H 3.002 F CF₃ H H 3.003 Cl CF₃ H H 3.004 Br CF₃ H H 3.005 CHF₂ CF₃ H H 3.006 CCl₃ CF₃ H H 3.007 CClF₂ CF₃ H H 3.008 CF₃ CF₃ H H 3.009 CH₃ CF₃ H H 3.01 CH₂CH₃ CF₃ H H 3.011 CH(CH₃)₂ CF₃ H H 3.012 (CH₂)₂CH₃ CF₃ H H 3.013 Ph CF₃ H H 3.014 CH₂F CF₃ H H 3.015 CH₂Cl CF₃ H H 3.016 CH₂Br CF₃ H H 3.017 CH₂OH CF₃ H H 3.018 CH₂OCOCH₃ CF₃ H H 3.019 CH₂OCOPh CF₃ H H 3.02 CH₂OCH₃ CF₃ H H 3.021 CH₂OCH₂CH₃ CF₃ H H 3.022 CH₂CH₂OCH₃ CF₃ H H 3.023 CH₂SMe CF₃ H H 3.024 CH₂SOMe CF₃ H H 3.025 CH₂SO₂Me CF₃ H H 3.026 CH₂SO₂Ph CF₃ H H 3.027 SCH₂Ph CF₃ H H 3.028 SOCH₂Ph CF₃ H H 3.029 SO₂CH₂Ph CF₃ H H 3.03 SCH₃ CF₃ H H 3.031 SOCH₃ CF₃ H H 3.032 SO₂CH₃ CF₃ H H 3.033 N(CH₃)₂ CF₃ H H 3.034 CH═CH₂ CF₃ H H 3.035 CH₂CH═CH₂ CF₃ H H 3.036 SO₂N(CH₃)₂ CF₃ H H 3.037 CCH CF₃ H H 3.038 OCH₃ CF₃ H H 3.039 OPh CF₃ K H 3.04 OCHF₂ CF₃ H H 3.041 CO₂Me CF₃ H H 3.042 OCH₂CCH CF₃ H H 3.043 OCH₂CF₃ CF₃ H H 3.044 H CF₃ H H 3.045 CN CF₃ H H 3.046 H CHF₂ H H 3.047 CH₃ CHF₂ H H 3.048 CH₂CH₃ CHF₂ H H 3.049 CH₂OCH₃ CHF₂ H H 3.05 H CF₂Cl H H 3.051 CH₃ CF₂Cl H H 3.052 CH₂CH₃ CF₂Cl H H 3.053 CH₂OCH₃ CF₂Cl H H 3.054 Cl CH₃ H H 3.055 CN SCH₃ H H 3.056 CN SO₂CH₃ H H

[0262] TABLE 4

Comp. No. R₁ R₂ R₃ R₄ R₅ P 4.001 H CF₃ H H OH 0 4.002 F CF₃ H H OH 0 4.003 Cl CF₃ H H OH 0 4.004 Br CF₃ H H OH 0 4.005 CHF₂ CF₃ H H OH 0 4.006 CCl₃ CF₃ H H OH 0 4.007 CClF₂ CF₃ H H OH 0 4.008 CF₃ CF₃ H H OH 0 4.009 CH₃ CF₃ H H OH 0 4.01 CH₂CH₃ CF₃ H H OH 0 4.011 CH(CH₃)₂ CF₃ H H OH 0 4.012 (CH₂)₂CH₃ CF₃ H H OH 0 4.013 C(CH₃)₃ CF₃ H H OH 0 4.014 Ph CF₃ H H OH 0 4.015 CH₂F CF₃ H H OH 0 4.016 CH₂Cl CF₃ H H OH 0 4.017 CH₂Br CF₃ H H OH 0 4.018 CH₂OH CF₃ H H OH 0 4.019 CH₂OCOCH₃ CF₃ H H OH 0 4.02 CH₂OCOPh CF₃ H H OH 0 4.021 CH₂OCH₃ CF₃ H H OH 0 4.022 CH₂OCH₂CH₃ CF₃ H H OH 0 4.023 CH₂CH₂OCH₃ CF₃ H H OH 0 4.024 CH₂SMe CF₃ H H OH 0 4.025 CH₂SOMe CF₃ H H OH 0 4.026 CH₂SO₂Me CF₃ H H OH 0 4.027 CH₂SO₂Ph CF₃ H H OH 0 4.028 N(CH₃)₂ CF₃ H H OH 0 4.029 CH═CH₂ CF₃ H H OH 0 4.03 CH₂CH═CH₂ CF₃ H H OH 0 4.031 SO₂N(CH₃)₂ CF₃ H H OH 0 4.032 CCH CF₃ H H OH 0 4.033 cyclopropyl CF₃ H H OH 0 4.034 OCH₃ CF₃ H H OH 0 4.035 OPh CF₃ H H OH 0 4.036 OCHF₂ CF₃ H H OH 0 4.037 CO₂Me CF₃ H H OH 0 4.038 OCH₂CCH CF₃ H H OH 0 4.039 H CF₃ H H OH 1 4.04 F CF₃ H H OH 1 4.041 Cl CF₃ H H OH 1 4.042 Br CF₃ H H OH 1 4.043 CHF₂ CF₃ H H OH 1 4.044 Cl₃ CF₃ H H OH 1 4.045 CClF₂ CF₃ H H OH 1 4.046 CF₃ CF₃ H H OH 1 4.047 CH₃ CF₃ H H OH 1 4.048 CH₂CH₃ CF₃ H H OH 1 4.049 CH(CH₃)₂ CF₃ H H OH 1 4.05 (CH₂)₂CH₃ CF₃ H H OH 1 4.051 C(CH₃)₃ CF₃ H H OH 1 4.052 Ph CF₃ H H OH 1 4.053 CH₂F CF₃ H H OH 1 4.054 CH₂Cl CF₃ H H OH 1 4.055 CH₂Br CF₃ H H OH 1 4.056 CH₂OH CF₃ H H OH 1 4.057 CH₂OCOCH₃ CF₃ H H OH 1 4.058 CH₂OCOPh CF₃ H H OH 1 4.059 CH₂OCH₃ CF₃ H H OH 1 4.06 CH₂OCH₂CH₃ CF₃ H H OH 1 4.061 CH₂CH₂OCH₃ CF₃ H H OH 1 4.062 CH₂SMe CF₃ H H OH 1 4.063 CH₂SOMe CF₃ H H OH 1 4.064 CH₂SO₂Me CF₃ H H OH 1 4.065 CH₂SO₂Ph CF₃ H H OH 1 4.066 N(CH₃₎ ₂ CF₃ H H OH 1 4.067 CH═CH₂ CF₃ H H OH 1 4.068 CH₂CH═CH₂ CF₃ H H OH 1 4.069 SO₂N(CH₃)₂ CF₃ H H OH 1 4.07 CCH CF₃ H H OH 1 4.071 cyclopropyl CF₃ H H OH 1 4.072 OCH₃ CF₃ H H OH 1 4.073 OPh CF₃ H H OH 1 4.074 OCHF₂ CF₃ H H OH 1 4.075 CO₂Me CF₃ H H OH 1 4.076 2-furyl CF₃ H H OH 1 4.077 OCH₂CCH CF₃ H H OH 1 4.078 H CF₂CF₃ H H OH 0 4.079 Cl CF₂CF₃ H H OH 0 4.08 CHF₂ CF₂CF₃ H H OH 0 4.081 CCl₃ CF₂CF₃ H H OH 0 4.082 CClF₂ CF₂CF₃ H H OH 0 4.083 CF₃ CF₂CF₃ H H OH 0 4.084 CH₃ CF₂CF₃ H H OH 0 4.085 CH₂CH₃ CF₂CF₃ H H OH 0 4.086 CH(CH₃)₂ CF₂CF₃ H H OH 0 4.087 (CH₂)₂CH₃ CF₂CF₃ H H OH 0 4.088 C(CH₃)₃ CF₂CF₃ H H OH 0 4.089 CH₂F CF₂CF₃ H H OH 0 4.09 CH₂Cl CF₂CF₃ H H OH 0 4.091 CH₂OH CF₂CF₃ H H OH 0 4.092 CH₂OCOCH₃ CF₂CF₃ H H OH 0 4.093 CH₂OCOPh CF₂CF₃ H H OH 0 4.094 CH₂OCH₃ CF₂CF₃ H H OH 0 4.095 CH₂OCH₂CH₃ CF₂CF₃ H H OH 0 4.096 CH₂SMe CF₂CF₃ H H OH 0 4.097 CH₂SOMe CF₂CF₃ H H OH 0 4.098 CH₂SO₂Me CF₂CF₃ H H OH 0 4.099 CH₂SO₂Ph CF₂CF₃ H H OH 0 4.1 N(CH₃)₂ CF₂CF₃ H H OH 0 4.101 CH═CH₂ CF₂CF₃ H H OH 0 4.102 CH₂CH═CH₂ CF₂CF₃ H H OH 0 4.103 SO₂N(CH₃)₂ CF₂CF₃ H H OH 0 4.104 CCH CF₂CF₃ H H OH 0 4.105 cyclopropyl CF₂CF₃ H H OH 0 4.106 OPh CF₂CF₃ H H OH 0 4.107 OCH₃ CF₂CF₃ H H OH 0 4.108 CO₂Me CF₂CF₃ H H OH 0 4.109 OCH₂CCH CF₂CF₃ H H OH 0 4.11 H CF₂CF₂CF₃ H H OH 0 4.111 CHF₂ CF₂CF₂CF₃ H H OH 0 4.112 CF₃ CF₂CF₂CF₃ H H OH 0 4.113 CH₃ CF₂CF₂CF₃ H H OH 0 4.114 CH₂CH₃ CF₂CF₂CF₃ H H OH 0 4.115 (CH₂)₂CH₃ CF₂CF₂CF₃ H H OH 0 4.116 CH₂Cl CF₂CF₂CF₃ H H OH 0 4.117 CH₂OCH₃ CF₂CF₂CF₃ H H OH 0 4.118 H CF₂Cl H H OH 0 4.119 Cl CF₂Cl H H OH 0 4.12 CHF₂ CF₂Cl H H OH 0 4.121 CCl₃ CF₂Cl H H OH 0 4.122 CClF₂ CF₂Cl H H OH 0 4.123 CF₃ CF₂Cl H H OH 0 4.124 CH₃ CF₂Cl H H OH 0 4.125 CH₂CH₃ CF₂Cl H H OH 0 4.126 CH(CH₃)₂ CF₂Cl H H OH 0 4.127 (CH₂)₂CH₃ CF₂Cl H H OH 0 4.128 C(CH₃)₃ CF₂Cl H H OH 0 4.129 CH₂F CF₂Cl H H OH 0 4.13 CH₂Cl CF₂Cl H H OH 0 4.131 CH₂OH CF₂Cl H H OH 0 4.132 CH₂OCOCH₃ CF₂Cl H H OH 0 4.133 CH₂OCOPh CF₂Cl H H OH 0 4.134 CH₂OCH₃ CF₂Cl H H OH 0 4.135 CH₂OCH₂CH₃ CF₂Cl H H OH 0 4.136 CH₂SMe CF₂Cl H H OH 0 4.137 CH₂SOMe CF₂Cl H H OH 0 4.138 CH₂SO₂Me CF₂Cl H H OH 0 4.139 CH₂SO₂Ph CF₂Cl H H OH 0 4.14 N(CH₃)₂ CF₂Cl H H OH 0 4.141 CH═CH₂ CF₂Cl H H OH 0 4.142 CH₂CH═CH₂ CF₂Cl H H OH 0 4.143 SO₂N(CH₃)₂ CF₂Cl H H OH 0 4.144 CCH CF₂Cl H H OH 0 4.145 cyclopropyl CF₂Cl H H OH 0 4.146 OPh CF₂Cl H H OH 0 4.147 OCH₃ CF₂Cl H H OH 0 4.148 CO₂Me CF₂Cl H H OH 0 4.149 OCH₂CCH CF₂Cl H H OH 0 4.15 CH₃ CF₂Cl H H OH 1 4.151 CH₂OCH₃ CF₂Cl H H OH 1 4.152 H CCl₃ H H OH 0 4.153 Cl CCl₃ H H OH 0 4.154 CH₃ CCl₃ H H OH 0 4.155 CH₂CH₃ CCl₃ H H OH 0 4.156 CH(CH₃)₂ CCl₃ H H OH 0 4.157 (CH₂)₂CH₃ CCl₃ H H OH 0 4.158 CH₂F CCl₃ H H OH 0 4.159 CH₂Cl CCl₃ H H OH 0 4.16 CH₂OH CCl₃ H H OH 0 4.161 CH₂OCOCH₃ CCl₃ H H OH 0 4.162 CH₂OCOPh CCl₃ H H OH 0 4.163 CH₂OCH₃ CCl₃ H H OH 0 4.164 CH₂OCH₂CH₃ CCl₃ H H OH 0 4.165 CH₂SMe CCl₃ H H OH 0 4.166 CH₂SOMe CCl₃ H H OH 0 4.167 CH₂SO₂Me CCl₃ H H OH 0 4.168 CH₂SO₂Ph CCl₃ H H OH 0 4.169 cyclopropyl CCl₃ H H OH 0 4.17 OPh CCl₃ H H OH 0 4.171 OCH₃ CCl₃ H H OH 0 4.172 CO₂Me CCl₃ H H OH 0 4.173 OCH₂CCH CCl₃ H H OH 0 4.174 CF₃ CHF₂ H H OH 0 4.175 CH₃ CHF₂ H H OH 0 4.176 CH₂OCH₃ CHF₂ H H OH 0 4.177 CH₂Cl CHF₂ H H OH 0 4.178 CH₂F CHF₂ H H OH 0 4.179 CF₃ CHF₂ H H OH 1 4.18 CH₃ CHF₂ H H OH 1 4.181 CH₂OCH₃ CHF₂ H H OH 1 4.182 CH₂Cl CHF₂ H H OH 1 4.183 CH₂F CHF₂ H H OH 1 4.184 CH₃ CF₃ H CH₃ OH 0 4.185 CH₃ CF₃ H CH₃ OH 1 4.186 Cl CF₃ H CH₃ OH 0 4.187 CH₃ CF₃ CH₃ H OH 0 4.188 CH₃ CF₃ Ph H OH 0 4.189 CH₃ CF₃ Cl H OH 0 4.19 CH₃ CF₃ CO₂CH₂CH₃ H OH 0 4.191 CH₃ CF₃ CO₂CH₂Ph H OH 0 4.192 CH₃ CF₃ CH₃ H OH 1 4.193 CH₃ CF₃ Ph H OH 1 4.194 CH₃ CF₃ Cl H OH 1 4.195 CH₃ CF₃ CO₂CH₂CH₃ H OH 1 4.196 CH₃ CF₃ OC₂CH₂Ph H OH 1 4.197 OCH₃ CF₃ CH₃ H OH 0 4.198 CH₂OCH₃ CF₃ CH₃ H OH 0 4.199 CH₂OCH₃ CF₃ Ph H OH 0 4.2 CH₂OCH₃ CF₃ Cl H OH 0 4.201 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 0 4.202 CH₂OCH₃ CF₃ CO₂CH₂Ph H OH 0 4.203 CH₂OCH₃ CF₃ CH₃ H OH 1 4.204 CH₂OCH₃ CF₃ Ph H OH 1 4.205 CH₂OCH₃ CF₃ Cl H OH 1 4.206 CH₂OCH₃ CF₃ CO₂CH₂CH₃ H OH 1 4.207 CH₂OCH₃ CF₃ CO₂CH₂Ph H OH 1 4.208 COOCH₃ H H H OH 0 4.209 CF₃ SCH₃ H H OH 0 4.21 CH₃ SCH₃ H H OH 0 4.211 CF₃ SOCH₃ H H OH 0 4.212 CH₃ SOCH₃ H H OH 0 4.213 CF₃ SO₂CH₃ H H OH 0 4.214 CH₃ SO₂CH₃ H H OH 0 4.215 CF₃ SCH₂CH₃ H H OH 0 4.216 CH₃ SCH₂CH₃ H H OH 0 4.217 CF₃ SOCH₂CH₃ H H OH 0 4.218 CH₃ SOCH₂CH₃ H H OH 0 4.219 CF₃ SO₂CH₂CH₃ H H OH 0 4.22 CH₃ SO₂CH₂CH₃ H H OH 0 4.221 CF₃ OCH₃ H H OH 0 4.222 CH₃ OCH₃ H H OH 0 4.223 CF₃ OCH₂CF₃ H H OH 0 4.224 CH₃ OCH₂CF₃ H H OH 0 4.225 CF₃ OCH₂CCH H H OH 0 4.226 CH₃ OCH₂CCH H H OH 0 4.227 CF₃ CN H H OH 0 4.228 CH₃ CN H H OH 0 4.229 CF₃ Cl H H OH 0 4.23 CH₃ Cl H H OH 0 4.231 H Cl H H OH 0 4.232 CF₃ OCH₃ H H OH 0 4.233 CH₃ OCH₃ H H OH 0 4.234 CF₃ CH₃ H H OH 0 4.235 H CF₃ H CH₃ OH 0 4.236 H CF₃ H CF₃ OH 0 4.237 H CF₃ H CH₂CH₃ OH 0 4.238 H CF₃ H CF₃ OH 0 4.239 H CF₃ H SCH₃ OH 0 4.24 H CF₃ H SOCH₃ OH 0 4.241 H CF₃ H SO₂CH₃ OH 0 4.242 H CF₃ H Cl OH 0 4.243 H CF₃ H OCH₃ OH 0 4.244 H CH₃ H CF₃ OH 0 4.245 H Cl H CF₃ OH 0 4.246 H OCH₃ H CF₃ OH 0 4.247 H SCH₃ H CF₃ OH 0 4.248 H SOCH₃ H CF₃ OH 0 4.249 CH₃ CF₃ H H S(CH₂)₇CH₃ 0 4.25 CH₃ CF₃ H H S(CH₂)₇CH₃ 0 4.251 CH₃ CF₃ H H SO(CH₂)₇CH₃ 0 4.252 CH₃ CF₃ H H SO₂(CH₂)₇CH₃ 0 4.253 CH₃ CF₃ H H SPh 0 4.254 CH₃ CF₃ H H SOPh 0 4.255 CH₃ CF₃ H H SO₂Ph 0 4.256 CH₃ CF₃ H H NOCH₃ 0 4.257 CH₃ CF₃ H H NOCH₂Ph 0 4.258 CH₃ CF₃ H H NOCH₂CH═CH₂ 0 4.259 CH₃ CF₃ H H NOC(CH₃)₃ 0 4.26 CH₃ CF₃ H H NOCH₂CH₃ 0 4.261 CH₃ CF₃ H H NCH₂CH₂SH 0 4.262 CH₃ CF₃ H H NN(CH₃)₂ 0 4.263 CH₃ CF₃ H H NN(CH₃)C(S)NH₂ 0 4.264 CH₃ CF₃ H H N-morpholino 0 4.265 CH₃ CF₃ H H NHCOCH₃ 0 4.266 CH₃ CF₃ H H NHCO(CH₂)₇CH₃ 0 4.267 CH₃ CF₃ H H NHCOPh 0 4.268 CH₃ CF₃ H H NHSO₂CH₃ 0 4.269 CH₃ CF₃ H H NH(CO)S(CH₂)₇CH₃ 0 4.27 CH₃ CF₃ H H Cl 0 4.271 CH₃ CF₃ H H NH₂ 0 4.272 CH₃ CF₃ H H OCOC(CH₃₎ ₃ 0 4.273 CH₃ CF₃ H H OCOCH₃ 0 4.274 CH₃ CF₃ H H OCOPh 0 4.275 CH₃ CF₃ H H OCO-cyclopropyl 0 4.276 CH₃ CF₃ H H OCOCH₂CH₃ 0 4.277 CH₃ CF₃ H H OCOCH═CH₂ 0 4.278 CH₃ CF₃ H H OCOCH═CHCH₃ 0 4.279 CH₃ CF₃ H H O(CO)SCH₃ 0 4.28 CH₃ CF₃ H H O(CO)S(CH₂)₇CH₃ 0 4.281 CH₃ CF₃ H H O(CO)OCH₂CH₃ 0 4.282 CH₃ CF₃ H H O(CO)N(CH₂CH₃)₂ 0 4.283 CH₃ (CF₂)₃CF₃ H H OH 0 4.284 CH₃ CF₃ H H S-(4-Cl-phenyl) 0 4.285 CH₃ CF₃ H H SO-(4-Cl-phenyl) 0 4.286 CH₃ CF₃ H H SO₂-(4-Cl-phenyl) 0 4.287 CH₃ CF₃ H H S-(4-CF₃-phenyl) 0 4288 CH₃ CF₃ H H SO-(4-CF₃-phenyl) 0 4.289 CH₃ CF₃ H H SO₂-(4-CF₃-phenyl) 0 4.29 CH₃ CF₃ H H S-(4-NO₂-phenyl) 0 4.291 CH₃ CF₃ H H SO-(4-NO₂-phenyl) 0 4.292 CH₃ CF₃ H H SO₂-(4-NO₂-phenyl) 0 4.293 CH₃ CF₃ H H

0 4.294 CH₃ CF₃ H H

0 4.295 CH₃ CF₃ H H

0 4.296 CH₃ CF₃ H H

0 4.297 CF₂H SCH₃ H H OH 0 4.298 CF₂Cl SCH₃ H H OH 0 4.299 CF₂H SOCH₃ H H OH 0 4.3 CF₂Cl SOCH₃ H H OH 0 4.301 CF₂H SO₂CH₃ H H OH 0 4.302 CF₂Cl SO₂CH₃ H H OH 0 4.303 CF₂H SCH₂CH₃ H H OH 0 4.304 CF₂Cl SCH₂CH₃ H H OH 0 4.305 CF₂H SOCH₂CH₃ H H OH 0 4.306 CF₂Cl SOCH₂CH₃ H H OH 0 4.307 CF₂H SO₂CH₂CH₃ H H OH 0 4.308 CF₂Cl SO₂CH₂CH₃ H H OH 0 4.309 CF₂H OCH₃ H H OH 0 4.31 CF₂Cl OCH₃ H H OH 0 4.311 CF₂H OCH₂CF₃ H H OH 0 4.312 CF₂Cl OCH₂CF₃ H H OH 0 4.313 CF₂H OCH₂CCH H H OH 0 4.314 CF₂Cl OCH₂CCH H H OH 0 4.315 CF₂H CN H H OH 0 4.316 CF₂Cl CN H H OH 0 4.317 CF₂H Cl H H OH 0 4.318 CF₂Cl Cl H H OH 0 4.319 CF₂H OCH₃ H H OH 0 4.32 CF₂Cl OCH₃ H H OH 0 4.321 CF₃ CH₂OCH₃ H H OH 0 4.322 CF₃ CH₂OCH₃ H H OH 1 4.323 CF₂Cl CH₂OCH₃ H H OH 0 4.324 CF₂Cl CH₂OCH₃ H H OH 1 4.325 CF₂H CH₂OCH₃ H H OH 0 4.326 CF₂H CH₂OCH₃ H H OH 1 4.327 CN CF₃ H H OH 0 4.328 SCH₃ H H H OH 0

[0263] TABLE 5

Comp. No. R₁ R₂ R₃ R₄ R₅ 5.001 H CF₃ H H CH₃ 5.002 F CF₃ H H CH₃ 5.003 Cl CF₃ H H CH₃ 5.004 CHF₂ CF₃ H H CH₃ 5.005 CCl₃ CF₃ H H CH₃ 5.006 CClF₂ CF₃ H H CH₃ 5.007 CF₃ CF₃ H H CH₃ 5.008 CH₃ CF₃ H H CH₃ 5.009 CH₂CH₃ CF₃ H H CH₃ 5.01 CH(CH₃)2 CF₃ H H CH₃ 5.011 (CH₂)₂CH₃ CF₃ H H CH₃ 5.012 CH₂F CF₃ H H CH₃ 5.013 CH₂Cl CF₃ H H CH₃ 5.014 CH₂Br CF₃ H H CH₃ 5.015 CH₂OCOCH₃ CF₃ H H CH₃ 5.016 CH₂OCH₃ CF₃ H H CH₃ 5.017 CH₂CH₂OCH₃ CF₃ H H CH₃ 5.018 CH₂SMe CF₃ H H CH₃ 5.019 CH₂SOMe CF₃ H H CH₃ 5.02 CH₂SO₂Me CF₃ H H CH₃ 5.021 N(CH₃)₂ CF₃ H H CH₃ 5.022 CH═CH₂ CF₃ H H CH₃ 5.023 CH₂CH═CH₂ CF₃ H H CH₃ 5.024 SO₂N(CH₃)₂ CF₃ H H CH₃ 5.025 CCH CF₃ H H CH₃ 5.026 cyclopropyl CF₃ H H CH₃ 5.027 OCH₃ CF₃ H H CH₃ 5.028 OPh CF₃ H H CH₃ 5.029 OCHF₂ CF₃ H H CH₃ 5.03 CO₂Me CF₃ H H CH₃ 5.031 OCH₂CCH CF₃ H H CH₃ 5.032 CF₃ SCH₃ H H CH₃ 5.033 CH₃ SCH₃ H H CH₃ 5.034 CF₃ SOCH₃ H H CH₃ 5.035 CH₃ SOCH₃ H H CH₃ 5.036 CF₃ SO₂CH₃ H H CH₃ 5.037 CH₃ SO₂CH₃ H H CH₃ 5.038 CF₃ OCH₃ H H CH₃ 5.039 CH₃ OCH₃ H H CH₃ 5.04 CF₃ OCH₂CF₃ H H CH₃ 5.041 CH₃ OCH₂CF₃ H H CH₃ 5.042 CF₃ OCH₂CCH H H CH₃ 5.043 CH₃ OCH₂CCH H H CH₃ 5.044 CF₃ CN H H CH₃ 5.045 CH₃ CN H H CH₃ 5.046 CF₃ Cl H H CH₃ 5.047 CH₃ Cl H H CH₃ 5.048 H Cl H H CH₃ 5.049 CF₃ OCH₃ H H CH₃ 5.05 CH₃ OCH₃ H H CH₃ 5.051 CF₃ CH₃ H H CH₃ 5.052 H CF₃ H CH₃ CH₃ 5.053 H CF₃ H CF₃ CH₃ 5.054 H CF₃ H CH₂CH₃ CH₃ 5.055 H CF₃ H CF₃ CH₃ 5.056 H CF₃ H SCH₃ CH₃ 5.057 H CF₃ H SOCH₃ CH₃ 5.058 H CF₃ H SO₂CH₃ CH₃ 5.059 H CF₃ H Cl CH₃ 5.06 H CF₃ H OCH₃ CH₃ 5.061 H CH₃ H CF₃ CH₃ 5.062 H Cl H CF₃ CH₃ 5.063 H OCH₃ H CF₃ CH₃ 5.064 H SCH₃ H CF₃ CH₃ 5.065 H SOCH₃ H CF₃ CH₃ 5.066 CF₂Cl CH₃ H H CH₃ 5.067 CF₂Cl CH₂CH₃ H H CH₃ 5.068 CF₂Cl SCH₃ H H CH₃ 5.069 CF₂Cl SOCH₃ H H CH₃ 5.07 CF₂Cl SO₂CH₃ H H CH₃ 5.071 CF₂Cl OCH₃ H H CH₃ 5.072 CF₂Cl OCH₂CF₃ H H CH₃ 5.073 CF₂Cl OCH₂CCH H H CH₃ 5.074 CF₂Cl CN H H CH₃ 5.075 CF₂Cl Cl H H CH₃ 5.076 CF₂Cl OCH₃ H H CH₃ 5.077 CF₃ CH₂OCH₃ H H CH₃ 5.078 CF₂Cl CH₂OCH₃ H H CH₃ 5.079 CF₂H CH₂OCH₃ H H CH₃ 5.08 CN CF₃ H H CH₃ 5.081 CH₃ CF₃ H H CH₂CH₃ 5.082 CH₃ CF₃ H H SCH₃ 5.083 CH₃ CF₃ H H SOCH₃ 5.084 CH₃ CF₃ H H SO₂CH₃ 5.085 CH₃ CF₃ H H H

[0264] TABLE 6

Comp. No. R₁ R₂ R₃ R₄ R₅ 6.001 Cl CF₃ H H CH₂CH₃ 6.002 CHF₂ CF₃ H H CH₂CH₃ 6.003 CCl₃ CF₃ H H CH₂CH₃ 6.004 CClF₂ CF₃ H H CH₂CH₃ 6.005 CF₃ CF₃ H H CH₂CH₃ 6.006 CH₃ CF₃ H H CH₂CH₃ 6.007 CH₂CH₃ CF₃ H H CH₂CH₃ 6.008 (CH₂)₂CH₃ CF₃ H H CH₂CH₃ 6.009 CH₂F CF₃ H H CH₂CH₃ 6.01 CH₂Cl CF₃ H H CH₂CH₃ 6.011 CH₂OCH₃ CF₃ H H CH₂CH₃ 6.012 CH₂SMe CF₃ H H CH₂CH₃ 6.013 CH₂SO₂Me CF₃ H H CH₂CH₃ 6.014 CH═CH₂ CF₃ H H CH₂CH₃ 6.015 CH₂CH═CH₂ CF₃ H H CH₂CH₃ 6.016 CCH CF₃ H H CH₂CH₃ 6.017 CF₃ SCH₃ H H CH₂CH₃ 6.018 CF₃ SOCH₃ H H CH₂CH₃ 6.019 CF₃ SO₂CH₃ H H CH₂CH₃ 6.02 CF₃ OCH₃ H H CH₂CH₃ 6.021 CF₃ CN H H CH₂CH₃ 6.022 CF₃ Cl H H CH₂CH₃ 6.023 CF₃ OCH₃ H H CH₂CH₃ 6.024 CF₃ CH₃ H H CH₂CH₃ 6.025 H CF₃ H CH₃ CH₂CH₃ 6.026 H CF₃ H CF₃ CH₂CH₃ 6.027 H CF₃ H SCH₃ CH₂CH₃ 6.028 H CF₃ H SOCH₃ CH₂CH₃ 6.029 H CF₃ H SO₂CH₃ CH₂CH₃ 6.03 H CF₃ H Cl CH₂CH₃ 6.031 H CF₃ H OCH₃ CH₂CH₃ 6.032 H CH₃ H CF₃ CH₂CH₃ 6.033 H Cl H CF₃ CH₂CH₃ 6.034 H OCH₃ H CF₃ CH₂CH₃ 6.035 CN CF₃ H H CH₂CH₃ 6.036 Cl CF₃ H H CH(CH₃)₂ 6.037 CHF₂ CF₃ H H CH(CH₃)₂ 6.038 CCl₃ CF₃ H H CH(CH₃)₂ 6.039 CClF₂ CF₃ H H CH(CH₃)₂ 6.04 CF₃ CF₃ H H CH(CH₃)₂ 6.041 CH₃ CF₃ H H CH(CH₃)₂ 6.042 CH₂CH₃ CF₃ H H CH(CH₃)₂ 6.043 (CH₂)₂CH₃ CF₃ H H CH(CH₃)₂ 6.044 CH₂F CF₃ H H CH(CH₃)₂ 6.045 CH₂Cl CF₃ H H CH(CH₃)₂ 6.046 CH₂OCH₃ CF₃ H H CH(CH₃)₂ 6.047 CH₂SMe CF₃ H H CH(CH₃)₂ 6.048 CH₂SO₂Me CF₃ H H CH(CH₃)₂ 6.049 CH═CH₂ CF₃ H H CH(CH₃)₂ 6.05 CH₂CH═CH₂ CF₃ H H CH(CH₃)₂ 6.051 CCH CF₃ H H CH(CH₃)₂ 6.052 CF₃ SCH₃ H H CH(CH₃)₂ 6.053 CF₃ SOCH₃ H H CH(CH₃)₂ 6.054 CF₃ SO₂CH₃ H H CH(CH₃)₂ 6.055 CF₃ OCH₃ H H CH(CH₃)₂ 6.056 CF₃ CN H H CH(CH₃)₂ 6.057 CF₃ Cl H H CH(CH₃)₂ 6.058 CF₃ OCH₃ H H CH(CH₃)₂ 6.059 CF₃ CH₃ H H CH(CH₃)₂ 6.06 H CF₃ H CH₃ CH(CH₃)₂ 6.061 H CF₃ H CF₃ CH(CH₃)₂ 6.062 H CF₃ H SCH₃ CH(CH₃)₂ 6.063 H CF₃ H SOCH₃ CH(CH₃)₂ 6.064 H CF₃ H SO₂CH₃ CH(CH₃)₂ 6.065 H CF₃ H Cl CH(CH₃)₂ 6.066 H CF₃ H OCH₃ CH(CH₃)₂ 6.067 H CH₃ H CF₃ CH(CH₃)₂ 6.068 H Cl H CF₃ CH(CH₃)₂ 6.069 H OCH₃ H CF₃ CH(CH₃)₂ 6.07 CN CF₃ H H CH(CH₃)₂ 6.071 Cl CF₃ H H HNPh 6.072 CHF₂ CF₃ H H HNPh 6.073 CCl₃ CF₃ H H HNPh 6.074 CClF₂ CF₃ H H HNPh 6.075 CF₃ CF₃ H H HNPh 6.076 CH₃ CF₃ H H HNPh 6.077 CH₂CH₃ CF₃ H H HNPh 6.078 (CH₂)₂CH₃ CF₃ H H HNPh 6.079 CH₂F CF₃ H H HNPh 6.08 CH₂Cl CF₃ H H HNPh 6.081 CH₂OCH₃ CF₃ H H HNPh 6.082 CH₂SMe CF₃ H H HNPh 6.083 CH₂SO₂Me CF₃ H H HNPh 6.084 CH═CH₂ CF₃ H H HNPh 6.085 CH₂CH═CH₂ CF₃ H H HNPh 6.086 CCH CF₃ H H HNPh 6.087 CF₃ SCH₃ H H HNPh 6.088 CF₃ SOCH₃ H H HNPh 6.089 CF₃ SO₂CH₃ H H HNPh 6.09 CF₃ OCH₃ H H HNPh 6.091 CF₃ CN H H HNPh 6.092 CF₃ Cl H H HNPh 6.093 CF₃ OCH₃ H H HNPh 6.094 CF₃ CH₃ H H HNPh 6.095 H CF₃ H CH₃ HNPh 6.096 H CF₃ H CF₃ HNPh 6.097 H CF₃ H SCH₃ HNPh 6.098 H CF₃ H SOCH₃ HNPh 6.099 H CF₃ H SO₂CH₃ HNPh 6.1 H CF₃ H Cl HNPh 6.101 H CF₃ H OCH₃ HNPh 6.102 H CH₃ H CF₃ HNPh 6.103 H Cl H CF₃ HNPh 6.104 H OCH₃ H CF₃ HNPh 6.105 CN CF₃ H H HNPh 6.106 Cl CF₃ H H HNC(CH₃)₃ 6.107 CHF₂ CF₃ H H HNC(CH₃)₃ 6.108 CCl₃ CF₃ H H HNC(CH₃)₃ 6.109 CClF₂ CF₃ H H HNC(CH₃)₃ 6.11 CF₃ CF₃ H H HNC(CH₃)₃ 6.111 CH₃ CF₃ H H HNC(CH₃)₃ 6.112 CH₂CH₃ CF₃ H H HNC(CH₃)₃ 6.113 (CH₂)₂CH₃ CF₃ H H HNC(CH₃)₃ 6.114 CH₂F CF₃ H H HNC(CH₃)₃ 6.115 CH₂Cl CF₃ H H HNC(CH₃)₃ 6.116 CH₂OCH₃ CF₃ H H HNC(CH₃)₃ 6.117 CH₂SMe CF₃ H H HNC(CH₃)₃ 6.118 CH₂SO₂Me CF₃ H H HNC(CH₃)₃ 6.119 CH═CH₂ CF₃ H H HNC(CH₃)₃ 6.12 CH₂CH═CH₂ CF₃ H H HNC(CH₃)₃ 6.121 CCH CF₃ H H HNC(CH₃)₃ 6.122 CF₃ SCH₃ H H HNC(CH₃)₃ 6.123 CF₃ SOCH₃ H H HNC(CH₃)₃ 6.124 CF₃ SO₂CH₃ H H HNC(CH₃)₃ 6.125 CF₃ OCH₃ H H HNC(CH₃)₃ 6.126 CF₃ CN H H HNC(CH₃)₃ 6.127 CF₃ Cl H H HNC(CH₃)₃ 6.128 CF₃ OCH₃ H H HNC(CH₃)₃ 6.129 CF₃ CH₃ H H HNC(CH₃)₃ 6.13 H CF₃ H CH₃ HNC(CH₃)₃ 6.131 H CF₃ H CF₃ HNC(CH₃)₃ 6.132 H CF₃ H SCH₃ HNC(CH₃)₃ 6.133 H CF₃ H SOCH₃ HNC(CH₃)₃ 6.134 H CF₃ H SO₂CH₃ HNC(CH₃)₃ 6.135 H CF₃ H Cl HNC(CH₃)₃ 6.136 H CF₃ H OCH₃ HNC(CH₃)₃ 6.137 H CH₃ H CF₃ HNC(CH₃)₃ 6.138 H Cl H CF₃ HNC(CH₃)₃ 6.139 H OCH₃ H CF₃ HNC(CH₃)₃ 6.14 CN CF₃ H H HNC(CH₃)₃

[0265] TABLE 7

Comp. No. R₁ R₂ R₃ R₄ p 7.001 H CF₃ H H 0 7.002 F CF₃ H H 0 7.003 Cl CF₃ H H 0 7.004 Br CF₃ H H 0 7.005 CHF₂ CF₃ H H 0 7.006 CCl₃ CF₃ H H 0 7.007 CClF₂ CF₃ H H 0 7.008 CF₃ CF₃ H H 0 7.009 CH₃ CF₃ H H 0 7.01 CH₂CH₃ CF₃ H H 0 7.011 CH(CH₃)₂ CF₃ H H 0 7.012 (CH₂)₂CH₃ CF₃ H H 0 7.013 C(CH₃)₃ CF₃ H H 0 7.014 Ph CF₃ H H 0 7.015 CH₂F CF₃ H H 0 7.016 CH₂Cl CF₃ H H 0 7.017 CH₂Br CF₃ H H 0 7.018 CH₂OH CF₃ H H 0 7.019 CH₂OCOCH₃ CF₃ H H 0 7.02 CH₂OCOPh CF₃ H H 0 7.021 CH₂OCH₃ CF₃ H H 0 7.022 CH₂OCH₂CH₃ CF₃ H H 0 7.023 CH₂CH₂OCH₃ CF₃ H H 0 7.024 CH₂SMe CF₃ H H 0 7.025 CH₂SOMe CF₃ H H 0 7.026 CH₂SO₂Me CF₃ H H 0 7.027 CH₂SO₂Ph CF₃ H H 0 7.028 SCH₃ CF₃ H H 0 7.029 SOCH₃ CF₃ H H 0 7.03 SO₂CH₃ CF₃ H H 0 7.031 N(CH₃)₂ CF₃ H H 0 7.032 CH═CH₂ CF₃ H H 0 7.033 CH₂CH═CH₂ CF₃ H H 0 7.034 SO₂N(CH₃)₂ CF₃ H H 0 7.035 CCH CF₃ H H 0 7.036 cyclopropyl CF₃ H H 0 7.037 OCH₃ CF₃ H H 0 7.038 OCHF₂ CF₃ H H 0 7.039 OCH₂CCH CF₃ H H 0 7.04 H CF₂CF₃ H H 0 7.041 Cl CF₂CF₃ H H 0 7.042 CHF₂ CF₂CF₃ H H 0 7.043 CCl₃ CF₂CF₃ H H 0 7.044 CClF₂ CF₂CF₃ H H 0 7.045 CF₃ CF₂CF₃ H H 0 7.046 CH₃ CF₂CF₃ H H 0 7.047 CH₂CH₃ CF₂CF₃ H H 0 7.048 CH(CH₃)₂ CF₂CF₃ H H 0 7.049 (CH₂)₂CH₃ CF₂CF₃ H H 0 7.05 C(CH₃)₃ CF₂CF₃ H H 0 7.051 CH₂F CF₂CF₃ H H 0 7.052 CH₂Cl CF₂CF₃ H H 0 7.053 CH₂OH CF₂CF₃ H H 0 7.054 CH₂OCOCH₃ CF₂CF₃ H H 0 7.055 CH₂OCOPh CF₂CF₃ H H 0 7.056 CH₂OCH₃ CF₂CF₃ H H 0 7.057 CH₂OCH₂CH₃ CF₂CF₃ H H 0 7.058 CH₂SMe CF₂CF₃ H H 0 7.059 CH₂SOMe CF₂CF₃ H H 0 7.06 CH₂SO₂Me CF₂CF₃ H H 0 7.061 CH₂SO₂Ph CF₂CF₃ H H 0 7.062 N(CH₃)₂ CF₂CF₃ H H 0 7.063 CH═CH₂ CF₂CF₃ H H 0 7.064 CH₂CH═CH₂ CF₂CF₃ H H 0 7.065 SO₂N(CH₃)₂ CF₂CF₃ H H 0 7.066 CCH CF₂CF₃ H H 0 7.067 cyclopropyl CF₂CF₃ H H 0 7.068 OCH₃ CF₂CF₃ H H 0 7.069 CO₂Me CF₂CF₃ H H 0 7.07 OCH₂CCH CF₂CF₃ H H 0 7.071 H CF₂Cl H H 0 7.072 Cl CF₂Cl H H 0 7.073 CHF₂ CF₂Cl H H 0 7.074 CCl₃ CF₂Cl H H 0 7.075 CClF₂ CF₂Cl H H 0 7.076 CF₃ CF₂Cl H H 0 7.077 CH₃ CF₂Cl H H 0 7.078 CH₂CH₃ CF₂Cl H H 0 7.079 CH(CH₃)₂ CF₂Cl H H 0 7.08 (CH₂)₂CH₃ CF₂Cl H H 0 7.081 C(CH₃)₃ CF₂Cl H H 0 7.082 CH₂F CF₂Cl H H 0 7.083 CH₂Cl CF₂Cl H H 0 7.084 CH₂OH CF₂Cl H H 0 7.085 CH₂OCOCH₃ CF₂Cl H H 0 7.086 CH₂OCOPh CF₂Cl H H 0 7.087 CH₂OCH₃ CF₂Cl H H 0 7.088 CH₂OCH₂CH₃ CF₂Cl H H 0 7.089 CH₂SMe CF₂Cl H H 0 7.09 CH₂SOMe CF₂Cl H H 0 7.091 CH₂SO₂Me CF₂Cl H H 0 7.092 CH₂SO₂Ph CF₂Cl H H 0 7.093 N(CH₃)₂ CF₂Cl H H 0 7.094 CH═CH₂ CF₂Cl H H 0 7.095 CH₂CH═CH₂ CF₂Cl H H 0 7.096 SO₂N(CH₃)₂ CF₂Cl H H 0 7.097 CCH CF₂Cl H H 0 7.098 cyclopropyl CF₂Cl H H 0 7.099 OCH₃ CF₂Cl H H 0 7.1 OCH₂CCH CF₂Cl H H 0 7.101 CF₃ CHF₂ H H 0 7.102 CH₃ CHF₂ H H 0 7.103 CH₂OCH₃ CHF₂ H H 0 7.104 CH₂Cl CHF₂ H H 0 7.105 CH₂F CHF₂ H H 0 7.106 CH₃ CF₃ H CH₃ 0 7.107 Cl CF₃ H CH₃ 0 7.108 CH₃ CF₃ CH₃ H 0 7.109 CH₃ CF₃ Cl H 0 7.11 OCH₃ CF₃ CH₃ H 0 7.111 CH₂OCH₃ CF₃ CH₃ H 0 7.112 CH₂OCH₃ CF₃ Cl H 0 7.113 COOCH₃ H H H 0 7.114 CF₃ SCH₃ H H 0 7.115 CH₃ SCH₃ H H 0 7.116 CF₃ SOCH₃ H H 0 7.117 CH₃ SOCH₃ H H 0 7.118 CF₃ SO₂CH₃ H H 0 7.119 CH₃ SO₂CH₃ H H 0 7.12 CF₃ OCH₃ H H 0 7.121 CH₃ OCH₃ H H 0 7.122 CF₃ OCH₂CF₃ H H 0 7.123 CH₃ OCH₂CF₃ H H 0 7.124 CF₃ OCH₂CCH H H 0 7.125 CH₃ OCH₂CCH H H 0 7.126 CF₃ CN H H 0 7.127 CH₃ CN H H 0 7.128 CF₃ Cl H H 0 7.129 CF₃ Cl H H 0 7.13 CH₃ Cl H H 0 7.131 H Cl H H 0 7.132 CF₃ OCH₃ H H 0 7.133 CH₃ OCH₃ H H 0 7.134 CF₃ CH₃ H H 0 7.135 H CF₃ H CH₃ 0 7.136 H CF₃ H CF₃ 0 7.137 H CF₃ H CH₂CH₃ 0 7.138 H CF₃ H CF₃ 0 7.139 H CF₃ H SCH₃ 0 7.14 H CF₃ H SOCH₃ 0 7.141 H CF₃ H SO₂CH₃ 0 7.142 H CF₃ H Cl 0 7.143 H CF₃ H OCH₃ 0 7.144 H CH₃ H CF₃ 0 7.145 H Cl H CF₃ 0 7.146 H OCH₃ H CF₃ 0 7.147 H SCH₃ H CF₃ 0 7.148 H SOCH₃ H CF₃ 0 7.149 CH₃ (CF₂)₃CF₃ H H 0 7.15 CF₂H SCH₃ H H 0 7.151 CF₂Cl SCH₃ H H 0 7.152 CF₂H SOCH₃ H H 0 7.153 CF₂Cl SOCH₃ H H 0 7.154 CF₂H SO₂CH₃ H H 0 7.155 CF₂Cl SO₂CH₃ H H 0 7.156 CF₂H OCH₃ H H 0 7.157 CF₂Cl OCH₃ H H 0 7.158 CF₂H OCH₂CF₃ H H 0 7.159 CF₂Cl OCH₂CF₃ H H 0 7.16 CF₂H OCH₂CCH H H 0 7.161 CF₂Cl OCH₂CCH H H 0 7.162 CF₂H CN H H 0 7.163 CF₂Cl CN H H 0 7.164 CF₂H Cl H H 0 7.165 CF₂Cl Cl H H 0 7.166 CF₂H OCH₃ H H 0 7.167 CF₂Cl OCH₃ H H 0 7.168 CF₃ CH₂OCH₃ H H 0 7.169 CF₂Cl CH₂OCH₃ H H 0 7.17 CF₂H CH₂OCH₃ H H 0 7.171 CN CF₃ H H 0 7.172 H CF₃ H H 2 7.173 F CF₃ H H 2 7.174 Cl CF₃ H H 2 7.175 Br CF₃ H H 2 7.176 CHF₂ CF₃ H H 2 7.177 CCl₃ CF₃ H H 2 7.178 CClF₂ CF₃ H H 2 7.179 CF₃ CF₃ H H 2 7.18 CH₃ CF₃ H H 2 7.181 CH₂CH₃ CF₃ H H 2 7.182 CH(CH₃)₂ CF₃ H H 2 7.183 (CH₂)₂CH₃ CF₃ H H 2 7.184 C(CH₃)₃ CF₃ H H 2 7.185 Ph CF₃ H H 2 7.186 CH₂F CF₃ H H 2 7.187 CH₂Cl CF₃ H H 2 7.188 CH₂Br CF₃ H H 2 7.189 CH₂OH CF₃ H H 2 7.19 CH₂OCOCH₃ CF₃ H H 2 7.191 CH₂OCOPh CF₃ H H 2 7.192 CH₂OCH₃ CF₃ H H 2 7.193 CH₂OCH₂CH₃ CF₃ H H 2 7.194 CH₂CH₂OCH₃ CF₃ H H 2 7.195 CH₂SMe CF₃ H H 2 7.196 CH₂SOMe CF₃ H H 2 7.197 CH₂SO₂Me CF₃ H H 2 7.198 CH₂SO₂Ph CF₃ H H 2 7.199 SCH₃ CF₃ H H 2 7.2 SOCH₃ CF₃ H H 2 7.201 SO₂CH₃ CF₃ H H 2 7.202 N(CH₃)₂ CF₃ H H 2 7.203 CH═CH₂ CF₃ H H 2 7.204 CH₂CH═CH₂ CF₃ H H 2 7.205 SO₂N(CH₃)₂ CF₃ H H 2 7.206 CCH CF₃ H H 2 7.207 cyclopropyl CF₃ H H 2 7.208 OCH₃ CF₃ H H 2 7.209 OCHF₂ CF₃ H H 2 7.21 OCH₂CCH CF₃ H H 2

[0266] TABLE 8

Comp. No. R₁ R₂ R₃ R₄ 8.001 H CF₃ H H 8.002 F CF₃ H H 8.003 Cl CF₃ H H 8.004 Br CF₃ H H 8.005 CHF₂ CF₃ H H 8.006 CCl₃ CF₃ H H 8.007 CClF₂ CF₃ H H 8.008 CF₃ CF₃ H H 8.009 CH₃ CF₃ H H 8.01 CH₂CH₃ CF₃ H H 8.011 CH(CH₃)₂ CF₃ H H 8.012 (CH₂)₂CH₃ CF₃ H H 8.013 C(CH₃)₃ CF₃ H H 8.014 Ph CF₃ H H 8.015 CH₂F CF₃ H H 8.016 CH₂Cl CF₃ H H 8.017 CH₂Br CF₃ H H 8.018 CH₂OH CF₃ H H 8.019 CH₂OCOCH₃ CF₃ H H 8.02 CH₂OCOPh CF₃ H H 8.021 CH₂OCH₃ CF₃ H H 8.022 CH₂OCH₂CH₃ CF₃ H H 8.023 CH₂CH₂OCH₃ CF₃ H H 8.024 CH₂SMe CF₃ H H 8.025 CH₂SOMe CF₃ H H 8.026 CH₂SO₂Me CF₃ H H 8.027 CH₂SO₂Ph CF₃ H H 8.028 SCH₃ CF₃ H H 8.029 SOCH₃ CF₃ H H 8.03 SO₂CH₃ CF₃ H H 8.031 N(CH₃)₂ CF₃ H H 8.032 CH═CH₂ CF₃ H H 8.033 CH₂CH═CH₂ CF₃ H H 8.034 SO₂N(CH₃)₂ CF₃ H H 8.035 CCH CF₃ H H 8.036 cyclopropyl CF₃ H H 8.037 OCH₃ CF₃ H H 8.038 OCHF₂ CF₃ H H 8.039 OCH₂CCH CF₃ H H

[0267] TABLE 9

Comp. No. R₁ R₂ R₃ R₄ 9.001 H CF₃ H H 9.002 F CF₃ H H 9.003 Cl CF₃ H H 9.004 Br CF₃ H H 9.005 CHF₂ CF₃ H H 9.006 CCl₃ CF₃ H H 9.007 CClF₂ CF₃ H H 9.008 CF₃ CF₃ H H 9.009 CH₃ CF₃ H H 9.01 CH₂CH₃ CF₃ H H 9.011 CH(CH₃)₂ CF₃ H H 9.012 (CH₂)₂CH₃ CF₃ H H 9.013 C(CH₃)₃ CF₃ H H 9.014 Ph CF₃ H H 9.015 CH₂F CF₃ H H 9.016 CH₂Cl CF₃ H H 9.017 CH₂Br CF₃ H H 9.018 CH₂OH CF₃ H H 9.019 CH₂OCOCH₃ CF₃ H H 9.02 CH₂OCOPh CF₃ H H 9.021 CH₂OCH₃ CF₃ H H 9.022 CH₂OCH₂CH₃ CF₃ H H 9.023 CH₂CH₂OCH₃ CF₃ H H 9.024 CH₂SMe CF₃ H H 9.025 CH₂SOMe CF₃ H H 9.026 CH₂SO₂Me CF₃ H H 9.027 CH₂SO₂Ph CF₃ H H 9.028 SCH₃ CF₃ H H 9.029 SOCH₃ CF₃ H H 9.03 SO₂CH₃ CF₃ H H 9.031 N(CH₃)₂ CF₃ H H 9.032 CH═CH₂ CF₃ H H 9.033 CH₂CH═CH₂ CF₃ H H 9.034 SO₂N(CH₃)₂ CF₃ H H 9.035 CCH CF₃ H H 9.036 cyclopropyl CF₃ H H 9.037 OCH₃ CF₃ H H 9.038 OCHF₂ CF₃ H H 9.039 OCH₂CCH CF₃ H H

[0268] Physical data (melting points in ° C.): Comp. No. 1.001 resin 1.005 crystals m.p. 61-62 1.008 oil 1.009 crystals m.p. 75-77 1.01  oil 1.011 crystals m.p. 111-112 1.012 crystals m.p. 87-88 1.013 crystals m.p. 112-114 1.014 oil 1.021 crystals m.p. 128-129 1.023 crystals m.p. 91-92 1.024 oil 1.026 amorphous 1.028 amorphous 1.03  resin 1.031 crystals m.p. 145-146 1.042 oil 1.043 crystals m.p. 107-110 1.047 crystals m.p. 155-156 1.048 viscous 1.05  crystals m.p. 51-53 1.06  crystals m.p. >220 1.109 oil 1.195 oil 1.258 crystals m.p. 119-121 1.31  crystals m.p. 92-94 1.312 viscous 1.313 crystals m.p. 137-138 1.314 oil 1.316 resin 1.323 oil 1.334 resin 1.335 crystals m.p. 140-142 1.339 crystals m.p. 137-139 1.341 resin 1.343 crystals m.p. 97-99 1.347 crystals m.p. 135-137 1.349 oil, n_(D) 1.4965 1.351 crystals m.p. 125-127 1.353 resin, n_(D) 1.5289 1.355 crystals m.p. 90-92 1.356 resin 1.358 resin 1.361 oil 1.362 crystals m.p. 139-142 1.371 crystals m.p. 96-97 1.372 resin 1.373 resin 1.374 crystals m.p. 116-1199 1.375 resin 1.376 crystals m.p. >270 1.381 crystals m.p. 117-118 1.383 crystals m.p. 172-173 1.384 resin 1.385 resin 1.386 resin 1.387 resin 1.388 crystals m.p. 102-104 1.389 crystals m.p. 143-145 1.39  crystals m.p. 195-197 1.391 solid 1.392 crystals m.p. 202-206 1.398 crystals m.p. 137-138 1.399 crystals m.p. 262-263 1.4  oil 1.401 oil 1.402 oil 1.403 oil 1.404 oil 1.405 viscous 1.406 oil 1.408 oil 1.409 oil 1.41  oil 1.411 crystals m.p. 98-100 1.412 crystals m.p. 130-131 1.413 crystals m.p. 167-170 1.414 crystals m.p. 166-167 1.415 crystals m.p. 91-93 1.418 crystals m.p. 149-150 1.421 crystals m.p. 88-89 1.422 crystals m.p. 175-177 1.423 crystals m.p. 45-47 1.424 crystals m.p. 102-104 2.001 resin 2.003 oil 2.03  crystals m.p. 107-110 2.038 crystals m.p. 111-113 2.043 resin 2.044 crystals m.p. 105-106 2.045 amorphous 3.001 crystals m.p. 95-97 3.054 oil 3.055 crystals m.p. 108-110 3.056 resin, D_(D) 1.5509 4.009 crystals m.p. 107-109 4.01  oil 4.011 oil 4.014 crystals m.p. 148-149 4.021 crystals m.p. 44-45 4.033 crystals m.p. 46-48 4.124 crystals m.p. 46-48 4.328 oil 5.008 resin 5.081 resin 5.083 crystals m.p. 161-162 5.084 crystals m.p. 215-216 5.085 resin 6.006 crystals m.p. 176-177 6.041 crystals m.p. 186-187 6.076 crystals m.p. 195-196 6.111 crystals m.p. 163-164 7.009 ratio A: B = 2:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.50; B: 2.66. 7.01  ratio A: B = 5:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.50; B: 2.64. 7.011 ratio A: B = 9:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.46; B: 2.59. 7.021 ratio A: B = 3:1. H-NMR(CDCl₃,ppm) SCH₃: A: 2.50; B: 2.62. 7.18  ratio A: B = 2:. H-NMR(CDCl₃,ppm) SO₂CH₃: A: 3.40; B: 3.58. 7.182 ratio A: B = 9:1. H-NMR(CDCl₃,ppm) SO₂CH₃: A: 3.32; B: 3.50. 7.192 ratio A: B = 3:1. H-NMR(CDCl₃,ppm) SO₂CH₃: A: 3.40; B: 3.58. 8.009 crystals m.p. 96-97 8.01  amorphous 8.011 oil 8.021 oil 9.009 crystals m.p. 112-113 9.01  amorphous 9.011 amorphous 9.021 oil

Biological Examples Example B1 Herbical action before emergence of the plants (pre-emergence action)

[0269] Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastic pots. Immediately after sowing, the test substances are sprayed on (500 l of water/ha) as an aqueous suspension (prepared from a 25% wettable powder (Example F3, b) according to WO 97/34485) or emulsion (prepared from a 25% emulsion concentrate (Example F1, c)), corresponding to a dosage of 2 kg of AS/ha. The test plants are then grown under optimum conditions in a greenhouse. After a test period of 3 weeks, the test is evaluated with a nine-level scale of ratings (1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action. TABLE B1 pre-emergence action: Active compound Test plant No. Avena Cyperus Setaria Sinapis Solanum Stellaria 1.009 2 1 1 2 1 2 1.376 2 1 1 2 1 2 4.009 1 2 1 2 1 3 7.009 4 2 1 3 1 2 1.381 4 1 2 2 1 1 1.011 2 1 1 1 1 1 5.008 2 1 1 2 1 2 4.021 2 1 2 2 1 2 1.010 2 1 1 1 1 2 1.021 4 2 1 1 1 3 1.398 2 1 1 1 1 1 1.195 2 1 1 1 1 2 4.124 2 1 2 2 1 2 1.411 3 2 1 2 1 2 1.042 4 2 2 1 1 4 1.023 2 2 2 1 1 2 1.109 2 2 2 2 1 3 1.313 3 1 2 1 1 2 1.401 2 1 1 2 1 2 1.404 2 1 1 2 1 2 1.400 2 1 1 2 1 2 1.403 2 1 1 1 1 2 1.405 2 1 1 1 1 2 1.406 2 1 1 1 1 2 1.402 2 1 1 2 1 2 1.005 4 1 1 1 1 1 1.043 4 2 1 2 1 2 1.409 1 1 1 1 1 1 1.41  2 1 1 1 1 1 1.06  2 1 1 2 1 1 7.192 4 2 2 3 2 2 7.021 1 1 1 1 1 1

[0270] The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.

Example B2 Post-emeroence Herbicidal Action

[0271] Monocotyledonous and dicotyledonous test plants are grown in plastic pots with standard soil in a greenhouse and, in the 4- to 6-leaf stage, are sprayed with an aqueous suspension of the test substances of the formula 1, prepared from a 25% wettable powder (Example F3, b) according to WO 97134485) or with an emulsion of the test substances of the formula I, prepared from a 25% emulsion concentrate (Example F1, c) according to WO 97/34485), corresponding to a dosage of 2 kg of AS/ha (500 l of water/ha). The test plants are then grown further under optimum conditions in a greenhouse. After a test period of about 18 days, the test is evaluated with a nine-level scale of rating (1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action. In this test, the compounds of the formula I show strong herbicidal action. TABLE B2 post-emergence action: Active compound Test plant No. Avena Setaria Solanum Sinapis Stellaria 1.009 1 1 1 1 2 1.376 1 2 2 1 2 4.009 1 1 1 1 1 1.026 3 1 1 1 2 7.009 3 2 1 1 1 1.381 2 2 2 2 2 1.011 2 2 2 2 2 5.008 2 3 1 1 2 5.085 3 2 2 1 2 4.021 2 2 1 1 2 1.012 3 2 2 1 2 1.010 2 2 2 1 4 4.010 3 3 2 2 2 1.021 2 4 2 1 2 1.398 2 2 2 1 2 1.195 2 2 2 1 2 4.124 2 2 1 1 2 1.411 2 2 2 1 2 1.008 2 2 2 1 2 6.006 2 5 2 2 2 5.081 3 2 1 1 2 1.042 2 2 2 1 2 1.023 2 2 2 1 2 1.109 2 2 2 1 2 1.313 2 2 2 1 2 1.401 2 2 2 2 2 1.404 2 2 1 1 2 1.400 2 2 2 1 2 1.403 2 2 2 1 2 1.403 2 2 2 1 2 1.405 2 2 2 1 2 1.406 2 2 1 1 2 1.402 2 2 2 1 2 1.001 3 2 2 1 2 1.005 2 2 2 1 2 1.362 3 2 2 1 2 1.043 2 2 2 1 2 1.409 2 1 1 1 2 1.410 1 1 1 1 1 1.060 2 1 1 1 2 7.192 2 3 3 2 2 7.021 1 2 1 1 2 1.048 2 1 1 1 2

[0272] The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.

Example B3 Herbicidal action before emergence of the plants (pre-emergence action)

[0273] Monocotyledonous and dicotyledonous test plants are sown in pots in standard soil. Immediately after sowing, the test substances are sprayed on (500 l of spray liquorlha) as an aqueous suspension, prepared from a wettable powder WP10 corresponding to the desired dosage (250 g of a.i./ha).

[0274] The test plants are then grown under optimum conditions in a greenhouse. After a test period of 3 weeks, the test is evaluated with a nine -evel scale of ratings (1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action, 7-9 mean good tolerance. TABLE B3 Pre-emergence action: Test plant Active Dose compound Abut- Amar- Cheno- [g of No. ilon anthus podium Kochia Sida Stellaria AS/ha] 1.355 1 1 1 1 2 2 250 1.347 2 2 1 1 4 1 250 1.335 1 2 1 5 2 7 250 1.349 1 3 1 4 2 5 250 1.339 2 1 1 7 2 1 250 1.341 3 9 1 9 4 1 250 1.343 1 4 1 9 3 5 250

[0275] The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485.

Example B4 Herbicidal action after the emergence of the plants ( post-emer gence action)

[0276] Monocotyledonous and dicotyledonous test plants are sown in pots in standard soil. In the 2-3- leaf stage of the test plants, the test substances are sprayed on (500 l of spray liquor/ha) as an aqueous suspension, prepared from a wettable powder WP10 according to the desired dosage (250 g of a.i./ha). 0.2% of X77 is added as wetting agent to the spray liquor. The test plants are then grown under optimum conditions in a greenhouse.

[0277] After a test period of 3 weeks, the test is evaluated with a nine4evel scale of ratings (1=complete damage, 9=no effect). Ratings of 1 to 4 (in particular 1 to 3) mean good to very good herbicidal action, 7-9 mean good tolerance. TABLE B4 Post-emergence action: Test plant Active Dose compound Abut- Amar- Cheno- [g of No. ilon anthus podium Kochia Sida Stellaria AS/ha] 1.355 2 2 2 3 2 3 250 1.347 3 2 2 2 3 3 250 1.335 3 2 2 2 2 3 250 1.349 2 2 2 2 2 3 250 1.339 2 2 3 1 4 3 250 1.351 5 2 3 3 3 3 250 1.341 5 2 3 4 5 4 250 1.343 3 2 2 3 9 3 250 1.361 2 2 2 2 2 3 250

[0278] The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8 according to WO 97/34485. 

What is claimed is:
 1. A compound of the formula I

in which each R independently is C₁-C₆alkyl, C₁-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆ haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C rhaloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkylamino, di-C₁-C₆ alkylamino, C₁-C₆alkylaminosulfonyl, di-C₁-C₆alkylaminosulfonyl, —N(R₁)—S—R₂, —N(R₃)—SO—R₄, —N(R₅)—SO₂—R₆, nitro, cyano, halogen, hydroxyl, amino, formyl, hydroxy-C₁-C₆alkyl, C₁-C₆ alkoxy-C₁-C₆alkyl, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkyl, C₁-C₆alkytthio-C₁-C₆alkyl, C₁-C₆ alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl, thiocyanato-C₁-C₆alkyl, cyano-C₁-C₆ alkyl, oxiranyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkoxy-C i-C₆alkoxy, cyano-C₁-C₆ alkenyloxy, C₁-C₆alkoxycarbonyloxy-C₁-C₆a ikoxy, C₃-C₆alkynyloxy, cyano-C₁-C₆lkoxy, C₁-C₆ alkoxycarbonyl-C₁-C₆alkoxy, C₁-C₆alkylthio-C₁-C₆alkoxy, alkoxycarbonyl-C₁-C₆alkylthio, alkoxycarbonyl-C₁-C₆alkylsulfinyl, alkoxycarbonyl-C₁-C₆alkylsulfonyl, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio, phenylsu lfinyl, phenyisulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, where the phenyl groups may be mono- or polysubs ttuted by halogen, methyl, ethyl, trifluoromethyl, methoxy or nitro, or R is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is either attached directly to the pyridine ring or attached to the pyridine ring via a C₁-C₄alkylene group, and where each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and where the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkeny fthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalky lthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂ alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₇, NR₈R₉, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; m is 1, 2,3 or 4; p is 0 or 1; R₁, R₃ and R₅ independently of one another are hydrogen or C₁-C₆alkyl; R₂ is NR₁₀R₁₁, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C ,-C₆haloalkyl, C₃-C₆alkenyl, C₃-C6 haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, G I-C₃haloalkoxy, halogen, cyano or nitro; R₄ is NR₁₂R₁₃, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆ haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₆is NR₁₄R₁₅, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₈ haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₃-C₆cycloalkyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₇ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₈, R₁₀, R₁₂ and R₁₄ independently of one another are hydrogen or C₁-C₆alkyl; R₉, R₁₁, R₁₃ and R₁₅ independently of one another are C₁-C₆alkyl or C₁-C₆alkoxy; Q is the group Q₁

in which R₁₆, R₁₇, R₁₈ and R₁₉ independently of one another are hydrogen, hydroxyl, C₁-C₄alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₄alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl)₂, C₁-C₆ alkoxy, cyano, nitro, halogen or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C_(l)-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄aIkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro, COOH or cyano; or two adjacent substituents from the group consisting of R₁₆, R₁₇, R₁₈ and R₁₉ form a C₂-C₆alkylene bridge; R₂₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆ alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsu lfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂ haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₃₇R₃₈N, R₇₁R₇₂NNH—, R₂₁R₂₂NC(O)O—, R₇₃R₇₄NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₃₉, C₁-C₄ haloalkyl-S(O)₂NR₄₀, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂ alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenyisulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄hatoalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro or cyano, or a group Ar₁-thio, Ar₂-sulfinyl, Ar₃-sulfonyl, —OCO—Ar₄ or NH—Ar₅ in which Ar₁, Ar₂, Ar₃, Ar₄ and Ar₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃₋-C₆haloalkenylthio, C₃-C₆alkyny fthio, C₂-C₅ alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₄₁, NR₄₂R₄₃, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R₄₁ is C₁-C₃alkoxy, C₂- C₄alkoxycarbonyl , C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃ haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₄₂ is hydrogen or C₁-C₆alkyl; R₄₃ is C₁-C₆alkyl or C₁-C₆alkoxy; R₂₁, R₃₇, R₃₉, R₄₀, R₇₁ and R₇₃ independently of one another are hydrogen or C₁-C₄alkyl; R₂₂, R₃₈, R₇₂ and R₇₄ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₂₁ and R₂₂ together or R₃₇ and R₃₈ together or R₇₁ and R₇₂ together or R₇₃ and R₇₄ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or are the group Q₂

in which Y is a chemical bond, an alkylene group A l, carbonyl, oxygen, sulfur, sulfinyl, suifonyl, —NHR₂₄₈ or NH(CO)R₂₄₉; A₁ is C(R₂₄₆R₂₄₇)m₀₁; A is C(R₂₄₄R₂₄₅)r; r and m₀₁ independently of one another are 0, 1 or 2; R₂₄₀ is hydrogen, methyl or C₁-C₃alkoxycarbonyl; R₂₄₁, R₂₄₂, R₂₄₃, R₂₄₄, R₂₄₅, R₂₄₆ and R₂₄₇ independently of one another are hydrogen, halogen or methyl, or R₂₄₃ together with an adjacent group R₂₄₅ or R₂₄₇ is a chemical bond; R₂₄₈ and R₂₄₉ independently of one another are hydrogen or C₁-C₄alkyl; R₂₃ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, CT-C₁₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆ alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂ haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alky l-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₄₄R₄₅N, R₇₅R₇₆NNH—, R₄₆R₄₇NC(O)O—, R₇₇R₇₈NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₄₈, C₁-C₄ haloalkyl-S(O)₂NR₄₉, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyioxy, C₁-C₁₂ alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocar6amoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzyisulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro or cyano, or a group Ar₆-thio, Arrsulfinyl, Ar₈-sulfonyl, —OCO—Ar₉ or NH—Ar₁₀ in which Ar₆, Ar₇, Ar₈, Ar₉ and Ar₁₀ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkyny toxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅ alkoxyalky tthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsu lfonyt, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₀, NR₅₁R₅₂, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R₅₀ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₅₁ is hydrogen or C₁-C₆alkyl; R₅₂ is C₁-C₆alkyl or C₁-C₆alkoxy; R₄₆, R₄₄, R₄₈, R₄₉, R₇₅ and R₇₇ independently of one another are hydrogen or C₁-C₄alkyl; R₄₇, R₄₅, R₇₆ and R₇₈ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₄₄ and R₄₅ together or R₄₆ and R₄₇ together or R₇₅ and R₇₆ together or R₇₇ and R₇₈ together are pyrro tidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; or are the group Q₃

in which R₂ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C,₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁ ₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆ alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁ ₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsultonyl, C₂-C₁₂ haloalkenylthio, C₂-C₁₂haloalkenyisu lfinyl, C₁-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄a lky lsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₅₃R₅₄N, R₇₉R₈₀NNH—, R₅₅R₅₆NC(O)O—, R₈₁R₈₂NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₅₇, C₁-C₄ haloalkyl-S(O)₂NR₅₈, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenyicarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂ alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsu lfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsu lfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro or cyano, or a group Ar₁₁-thio, Ar₁₂-sulfinyl, Ar₁₃-sulfonyl, —OCO—Ar₁₄ or NH—Ar₁₅ in which Ar₁₁, Ar₁₂, Ar₁₃, Ar₁₄ and Ar₁₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅ alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsu ffonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₅₉, NR₆₀R₆₁, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R₅₉ is C₁-C₃alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₆₀ is hydrogen or C₁-C₆alkyl; R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy; R₅₅, R₅₃, R₅₇, R₅₈, R₇₉ and R₈₁ independently of one another are hydrogen or C₁-C₄alkyl; R₅₆, R₅₄, R₈₀ and R₈₂ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₅₃ and R₅₄ together or R₅₅ and R₅₆ together or R₇₉ and R₈₀ together or R₈₁ and R₈₂ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; R₂₉ is hydrogen, C₁-C₆alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, (C₁-C₄alkyl)NHCO, phenylaminocarbonyl, benzylaminocarbonyl or (C₁-C₄alkyl)₂NCO, where the phenyl and benzyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄ alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄ alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano; or is the group Q₄

in which R₃₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁ ₂alkyisulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂ haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆ alkylsu ifinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁ ₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂ alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C,₂alkynylsulfonyl, C₂-C₁₂ haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₆₂R₆₃N, R₈₃R₈₄NNH—, R₆₄R₆₅NC(O)—, R₈₅R₈₆NC(O)NH—, C₁-C₄alkyl-S(O)₂NR₆₆, C₁-C₄ haloalkyl-S(O)₂NR₆₇, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁ ₈alkylcarbonyloxy, where the alkyl group may be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂ alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may each be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄ alkyl), halogen, nitro or cyano, or a group Ar₁₆-thio, Ar₁₇sulfinyl, Ar₁₈-sulfonyl, —OCO—Ar₁₉ or NH—Ar₂₀ in which Ar₁₆, Ar₁₇, Ar₁₈, Ar₁₉ and Ar₂₀ independently of one another are a five- to ten-me mbered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and in which each ring system may not contain more than 2 oxygen atoms and not more than two sulfur atoms, and in which the ring system for its part may be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅ alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsu lfonyl, C ,-C₆haioalkyisulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, C₁-C₃alkylene-R₆₈, NR₆₉R₇₀, halogen, cyano, nitro, phenyl and benzylthio, where phenyl and benzylthio for their part may be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are different from halogen; R₆₈ is C₁-C₃alkoxy, C₂C₄alkoxycarbonylt, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or phenyl, where phenyl for its part may be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃ alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R₇₀ is hydrogen or C₁-C₆alkyl; R₆₁ is C₁-C₆alkyl or C₁-C₆alkoxy; R₆₄, R₆₂, R₆₆, R₆₇, R₈₃ and R₈₅ independently of one another are hydrogen or C₁-C₄alkyl; R₆₅, R₆₃, R₈₄ and R₈₆ independently of one another are hydrogen, C₁-C₁₂alkyl, hydroxyl, C₁-C₁₂alkoxy, C₃-C₆alkenyloxy or C₃-C₆alkynyloxy; or R₆₂ and R₆₃ together or R₆₄ and R₆₅ together or R₈₃ and R₈₄ together or R₈₅ and R₈₆ together are pyrrolidino, piperidino, morpholino, thiomorpholino, which may be mono- or polysubstituted by methyl groups; R₃₃ and R₃₄ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₁-C₄alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄ alkyl-NHS(O)₂, C₁-C₄haloalkyl, —NH—C₁-C₄alkyl, —N(C₁-C₄alkyl )₂, C₁-C₆alkoxy or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C,-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₆ alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄ alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or R₃₃ and R₃₄ together forrn a C₂-C₆alkylene bridge; and R₃₅ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl or benzyl, which for its part may be substituted by halogen, methyl or methoxy, or is C₁-C₄alkoxycarbonyl or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-c₄alkyl-s(o)₂O, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloaikyi-s(o)₂o, C i-C₄alkyl-S(O)₂NH, C₁-C₄ alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or is the group Q₅

in which Z is S, SO or SO₂; R₀₁ is hydrogen, C₁-C₈alkyl, C₁-C₈alkyl substituted by halogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, —CO₂R₀₂, —COR₀₃, —COSR₀₄, —NR₀₅R₀₆, CONR₀₃₆R₀₃₇ or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄ alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl )C₁-CAalkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄ aikyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇ cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₂₅R₂₆, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsultonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₁₅CO₂R₀₂₇; or R₀₁ is C₂-C₈alkenyl or C₂-C₈alkenyl substituted by halogen, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, —CONR₀₃₂R₀₃₃, cyano, nitro, —CHO, —CO₂R₀₃₈, —COR₀₃₉, —COS—C₁-C₄alkyl, —NR₀₃₄R₀₃₅ or phenyl which for its part may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alky fthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄ alkyl, N(C₁-C₆alkyl)SO₂-phenyt, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C ralkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄ alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₄₀R₀₄₁, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄ haioalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄ alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₄₃CO₂R₀₄₂; or R₀₁ is C₃-C₆alkynyl or C₃-C₆alkynyl substituted by halogen, C₁-C₄haloalkyl, cyano, —CO₂R₀₄₄ or phenyl, which for its part may be substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C_(l)-C₄ alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄ alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄ alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyI)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OS₂O-C₁-C₄ alkyl, CONR₀₂₈R₀₂₉, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₃₁CO₂R₀₃₀; or R₀₁ is C₃-C₇cycloalkyl, C₃-C₁cycloalkyl substituted by C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or phenyl, which for its part may be substituted by halogen, nitro, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkyl and C₁-C₄haloalkyl; or R₀₁ is C₁-C₄alkylene-C₃-C₇cycloalkyl, phenyl, or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsul tonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂-C₁-C₄ alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄ alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂—C₁-C₄alkyl, CONR₀₄₅R₀₄₆, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄ haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄ alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, or —NR₀₄₈CO₂R₀₄₇; or R₀₁ is C₁-C₄alkylene-phenyl, COR₀₇ or 4-6-membered heterocyclyl; R₀₂, R₀₃₈, R₀₄₄ and R₀₆₆ independently of one another are hydrogen, C₁-C₄alkyl, phenyl, or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C i-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, Coophenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄ alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyi)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆ alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄a lkyl, N(C₃-C₆ alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇Cyloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₄₉R₀₅₀, OSO₂—C₁-C₄ haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₅₂CO₂R₀₅₃; R₀₃, R₀₃₉ and R₀₆₇ independently of one another are C₁-C₄alkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C ,-C₄haloalkoxy, C₂-C₆alkenyl, C₃-C₆ alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)S)₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO₂-phenyl, N(C₃-C₇ cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂-C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₇₀R₀₅₄, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₅₆CO₂R₀₅₅; R₀₄ is C₁-C₄alkyl; R₀₅ is hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆ alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄ alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)-C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alkyl, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆ alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂H, N(C₃-C₆ alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆alkynyl)SO ~phenyl, N(C₃-C₇cycloalkyl)SO₂H, N(C₃-C₇ cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OSO₂-C₁-C₄alkyl, CONR₀₅₇R₀₅₈, OSO₂—C₁-C₄haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄ha hoalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenyisu f finyl, C₁-C₄alkylenephenyl or —NR₀₆₀CO₂R₀₅₉; R₀₆ is hydrogen, C₁-C₄alkyl, C₂-C₆aikenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₆ alkenyl, C₃-C₆alkynyl, C₃-C₆alkenyloxy, C₃-C₆alkyny loxy, halogen, nitro, cyano, —COOH, COOC₁-C₄alkyl, COOphenyl, C₁-C₄alkoxy, phenoxy, (C₁-C₄alkoxy)-C₁-C₄alkyl, (C₁-C₄ alkylthio)-C₁-C₄alkyl, (C₁-C₄alkylsulfinyl)C₁-C₄alkyl, (C₁-C₄alkylsulfonyl)-C₁-C₄alkyl, NHSO₂—C₁-C₄alkyl, NHSO₂-phenyl, N(C₁-C₆alkyl)SO₂—C₁-C₄alky l, N(C₁-C₆alkyl)SO₂-phenyl, N(C₂-C₆ alkenyl)SO₂—C₁-C₄alkyl, N(C₂-C₆alkenyl)SO₂-phenyl, N(C₃-C₆alkynyl)SO₂—C₁-C₄alkyl, N(C₃-C₆ alkynyl)SO₂-phenyl, N(C₃-C₇cycloalkyl)SO₂—C₁-C₄alkyl, N(C₃-C₇cycloalkyl)SO₂-phenyl, N(phenyl)SO₂—C₁-C₄alkyl, N(phenyl)SO₂-phenyl, OS₀ ₂-C₁-C₄alkyl, CONR₀₆₁R₀₆₂, OSO₂—C₁-C₄ haloalkyl, OSO₂-phenyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, phenylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, phenylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkylsulfinyl, phenylsulfinyl, C₁-C₄alkylene-phenyl or —NR₀₆₄CO₂R₀₆₃; R₀₇ is phenyl, substituted phenyl, C₁-C₄alkyl, C₁-C₄alkoxy or —NR₀₈R₀₉; R₀₈ and R₀₉ independently of one another are C₁-C₄alkyl, phenyl or phenyl which is substituted by halogen, nitro, cyano, C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄thioalkyl, —CO₂R₀₆₆, —COR₀₆₇, C₁-C₄alkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄haloalkyl; or R₀₈ and R₀₉ together form a 5-6-membered ring which may be interrupted by oxygen, NR₀₆₅ or S, R₀₁₅, R₀₃₁, R₀₄₃, R₀₄₈, R₀₅₂, R₀₅₆, R₀₆₀ and R₀₆₄ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl or C₃-C₇cycloalkyl; R₀₂₅, R₀₂₆, R₀₂₇, R₀₂₈, R₀₂₉, R₀₃₀, R₀₃₂, R₀₃₃, R₀₃₄, R₀₃₅, R₀₃₆, R₀₃₇, R₀₄₀, R₀₄₁, R₀₄₂, R₀₄₅, R₀₄₆, R₀₄₇, R₀₄₉, R₀₅₀, R₀₅₃, R₀₅₄, R₀₅₅, R₀₅₇, R₀₅₈, R₀₅₉, R₀₆₁, R₀₆₂, R₀₆₃, R₀₆₅ and R₀₇₀ independently of one another are hydrogen, C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, phenyl, or phenyl which is substituted by halogen, nitro, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkyl or C₁-C₄haloalkyl; and R₃₆ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆ haloalkynyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl which is substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆aIkynyl, C₃-C₆haloalkynyt, C₁-C₄ alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylcarbonyl, di-C₁-C₄alkylamino, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O or phenyl which for its part may be substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, cyano, nitro or COOH; and agronomically acceptable salts M⁺ and all stereoisomers and tautomers of the compounds of the formula I.
 2. A compound of the formula IIa

in which Q_(a) is hydroxyl, halogen, cyano or a group —CH₂(CO)R₃₆ or

R_(b) is hydrogen, C₁-₄alkyl or halogen; R_(f) is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoro-n-propyl or trichloromethyl; R_(a) is C₁-3aIkyl, C₁-C₃haloalkyl, C_(3 .)C₄cycloalkyl, C₁-C₂alkoxy-C₁-C₄alkyl, C₁-C₂ alkythiomethyl, hydroxyl, halogen, cyano, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl or C₁-C₃alkylsulfonyloxy, and R₀₁ and R₃₆ are defined as under group Q₅ of the formula 1, except for the compounds 2,6-bis-trifluoromethyinicotinic acid, 2,6-bis-trifluoromethyl-5-methoxynicotinic acid and 2-hydroxy-6-trifluoromethyinicotinic acid.
 3. A compound of the formula IIb

in which Q_(b) is hydroxyl, halogen, cyano, or a group —CH₂(CO)R₉₉ or

R₉₉ is C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₄cycloalkyl or C₁-C₄alkoxy; R_(f) is trifluoromethyl, difluorochloromethyl, pentafluoroethyl or heptafluoro-n-propyl; and R_(c) is C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₂a lkoxymethyl, C₁-C₂alkylthiomethyl, hydroxyl, halogen, cyano, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃alkylsulfonyl or C₁-C₃alkylsulfonyloxy and R₀₁ is as defined under formula I.
 4. A herbicidal and plant-growth-inhibiting composition, which contains a herbicidally effective amount of a compound of the formula I on an inert carrier.
 5. A method for controlling undesirable plant growth, wherein a herbicidally effective amount of an active compound of the formula I or a composition which contains this active compound is applied to the plants or their habitat.
 6. A method for inhibiting plant growth, wherein a herbicidally effective amount of an active compound of the formula I or a composit ion which contains this active compound is applied to the plants or their habitat.
 7. The use of a composition according to claim 4 for controlling undesirable plant growth. 